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TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xvii V. LIST OF ABBREVIATIONS Abbreviation Chemical Name Chemical Structure 18-Cr-6 18-crown-6 O O O O O O Ac acetyl O acac acetylacetonyl OO AA asymmetric aminohydroxylation NA AD asymmetric dihydroxylation NA ad adamantyl ADDP 1,1-(azodicarbonyl)dipiperidine NN N O O N ADMET acyclic diene metathesis polymerization NA acaen N,N-bis(1-methyl-3-oxobutylidene)ethylenediamine N N O O AIBN 2,2-azo bisisobutyronitrile NN N N Alloc allyloxycarbonyl OO Am amyl (n-pentyl) An p-anisyl O ANRORC anionic ring-opening ring-closing NA aq aqueous NA AQN anthraquinone O O Ar aryl (substituted aromatic ring) NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xviii Abbreviation Chemical Name Chemical Structure ATD aluminum tris(2,6-di-tert-butyl-4-methylphenoxide) OAl 3 atm1 atmosphere = 105 Pa (pressure) NA ATPH aluminum tris(2,6-diphenylphenoxide) O Ph Ph Al 3 BBN (9-BBN) 9-borabicyclo3.3.1nonane (9-BBN) B H B 9-borabicyclo3.3.1nonyl B BCMEbis(chloromethyl)ether OClCl BCNN-benzyloxycarbonyloxy-5-norbornene-2,3- dicarboximide O N O O O O BDPP(2R, 4R) or (2S, 4S) bis(diphenylphosphino)pentane (R)(R) Ph2PPPh2 BERborohydride exchange resin NA BHT2,6-di-t-butyl-p-cresol (butylated hydroxytoluene) OH BICP2(R)-2(R)-bis(dipenylphosphino)-1(R),1(R)- dicyclopentane (R) (R)(R) (R) Ph2PPPh2 BINAL-H 2,2-dihydroxy-1,1-binaphthyl lithium aluminum hydride O O Al H H Li BINAP 2,2-bis(diphenylphosphino)-1,1-binaphthyl PPh2 PPh2 TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xix Abbreviation Chemical Name Chemical Structure BINOL1,1-bi-2,2-naphthol OH OH Bipbiphenyl-4-sulfonyl S O O bipy 2,2-bipyridyl NN BLA Brnsted acid assisted chiral Lewis acid NA bmin1-butyl-3-methylimidazolium cation NN BMSBorane-dimethyl sulfide complex H3BSMe2 Bnbenzyl BNAH 1-benzyl-1,4-dihydronicotinamide N O NH2 BOB4-benzyloxybutyryl O O Boct-butoxycarbonyl OO BOMbenzyloxymethyl O BOP-Clbis(2-oxo-3-oxazolidinyl)phosphinic chloride P OCl O N O O N O bpboiling point NA BPDbis(pinacolato)diboron O O BB O O BPObenzoyl peroxide O O Ph O Ph O BPS (TBDPS) t-butyldiphenylsilyl Si TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xx Abbreviation Chemical Name Chemical Structure BQbenzoquinone OO Bsbrosyl = (4-bromobenzenesulfonyl) SBr O O BSA N,O-bis(trimethylsilyl)acetamide O NSiSi BSA Bovine serum albumin NA Bt1- or 2-benzotriazolyl N N N BTAF benzyltrimethylammonium fluoride N F BTEA benzyltriethylammonium N BTEAC benzyltriethylammonium chloride N Cl BTFP3-bromo-1,1,1-trifluoro-propan-2-one O F F F Br BTMA benzyltrimethylammonium N BTMSA bis(trimethylsilyl) acetylene SiSi BTSbis(trimethylsilyl) sulfate S O O O O SiSi BTSA benzothiazole 2-sulfonic acid S N S O O HO BTSPbis(trimethylsilyl) peroxide O OSi Si Bzbenzoyl O Bu (nBu)n-butyl ccyclo NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxi Abbreviation Chemical Name Chemical Structure cacirca (approximately) NA CA chloroacetyl O Cl CAN cerium(IV) ammonium nitrate (cericammonium nitrate) Ce(NH4)2(NO3)6 cat.catalytic NA CBcatecholborane O HB O CBSCorey-Bakshi-Shibata reagent N B O H Ph Ph R R = H, alkyl Cbz (Z) benzyloxycarbonyl O O cc. or conc. concentrated NA CCEconstant current electrolysis NA CDIcarbonyl diimidazole O N N N N CHD1,3 or 1,4-cyclohexadiene 1,3-CHD1,4-CHD CHIRAPHOS 2,3-bis(diphenylphosphino)butane (S) (S) P Ph Ph P Ph Ph Chx (Cy) cyclohexyl CIP2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate NHN Cl PF6 CM (XMET) cross metathesis NA CMMPcyanomethylenetrimethyl phosphorane P N COD1,5-cyclooctadiene COT1,3,5-cyclooctatriene Cpcyclopentadienyl CPTScollidinium-p-toluenesulfonate NH S O O O TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxii Abbreviation Chemical Name Chemical Structure CRA complex reducing agent NA Cr-PILCchromium-pillared clay catalyst NA CSA camphorsufonic acid O SO3H CSIchlorosulfonyl isocyanate Cl S O O N C O CTAB cetyl trimethylammonium bromide NBr CTACl cetyl trimethylammonium chloride N C15H31 Cl CTAP cetyl trimethylammonium permanganate N C15H31 MnO4 heat NA ddays (length of reaction time) NA DABCO 1,4-diazabicyclo2.2.2octane N N N N DAST diethylaminosulfur trifluoride SN F F F DATMP diethylaluminum 2,2,6,6-tetramethylpiperidide N AlEt2 DBA (dba) dibenzylideneacetone O Ph Ph DBAD di-tert-butylazodicarboxylate N NO O O O DBIdibromoisocyanuric acid N O N O NH OBr Br TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxiii Abbreviation Chemical Name Chemical Structure DBMdibenzoylmethane OO DBN1,5-diazabicyclo4.3.0non-5-ene N N 1 2 3 4 5 6 7 8 9 DBSdibenzosuberyl DBU1,8-diazabicyclo5.4.0undec-7-ene N N 1 2 3 4 5 6 7 8 9 10 11 DCA 9,10-dicyanoanthracene CN CN DCB1,2-dichlorobenzene Cl Cl DCCdicyclohexylcarbodiimide N C N DCE1,1-dichloroethane Cl Cl DCMdichloromethane CH2Cl2 DCN1,4-dicyanonaphthalene CN CN Dcpmdicyclopropylmethyl DCUN,N-dicyclohexylurea N H O N H DDQ2,3-dichloro-5,6-dicyano-1,4-benzoquinone O O NC NCCl Cl de diastereomeric excess NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxiv Abbreviation Chemical Name Chemical Structure DEAD diethyl azodicarboxylate N N O O O O DEIPSdiethylisopropylsilyl Si DEPBT3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin- 4(3H)-one N N N O O P OEt EtO O DETdiethyl tartrate OH HO (R) (R) O O O O DHP3,4-dihydro-2H-pyran O DHQdihydroquinine N N H OH OMe H (DHQ)2PHAL bis(dihydroquinino)phthalazine N MeO N Et H O NN O N H Et H N OMe H DHQDdihydroquinidine N OMe H OH NH (DHQD)2PHAL bis(dihydroquinidino)phthalazine N OMe N H O NN O N H H N MeO H Et Et DIAD diisopropyl azodicarboxylate N NO O O O DIB (BAIB or PIDA) (diacetoxyiodo)benzene I O O O O TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxv Abbreviation Chemical Name Chemical Structure DIBAL (DIBAH) DIBAL-H diisobutylaluminum hydride Al H DICdiisopropyl carbodiimide N C N diop4,5-bis-(diphenylphosphanyl)methyl-2,2-dimethyl- 1,3dioxolane (R) (R) O O PPh2 PPh2 DIPAMP 1,2-bis(o-anisylphenylphosphino)ethane P O P O DIPEA (Hnigs base) diisopropylethylamine N DIPTdiisopropyl tartrate OH HO (R) (R) O O O O DLPdilauroyl peroxide O OC10H21 O C10H21 O DMA (DMAC) N,N-dimethylacetamide O N DMAD dimethyl acetylene dicarboxylate O OO O DMAP N,N-4-dimethylaminopyridine NN DMBm-dimethoxybenzene OO DMDOdimethyl dioxirane O O DME1,2-dimethoxyethane O O TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxvi Abbreviation Chemical Name Chemical Structure DMFN,N-dimethylformamide ON H DMI1,3-dimethylimidazolidin-2-one NN O DMPDess-Martin periodinane I O O AcO OAc OAc DMPSdimethylphenylsilyl Si DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (N,N-dimethyl propylene urea) N N O DMTSFdimethyl(methylthio)sulfonium tetrafluoroborate Me S S Me Me BF4 DMSdimethylsulfide S DMSOdimethylsulfoxide S O DMT4,4-dimethoxytrityl OO DMTMM 4-(4,6-dimethoxy1,3,5triazin-2-yl)-4- methylmorpholinium chloride N O N N N O O Cl DMTr4,4-dimethyltrityl DMTST(dimethylthio)methylsulfonium trifluoromethanesulfonate S S S S O O O F F F DNA deoxyribonucleic acid NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxvii Abbreviation Chemical Name Chemical Structure DPA (DIPA) diisopropylamine N H DPBP2,2-bis(diphenylphosphino)biphenyl (S) Ph2PPPh2 DPDCdiisopropyl peroxydicarbonate O OO O O O DPDMdiphenyl diazomethane N+ N- DPEDA 1,2-diamino-1,2-diphenylethane (R)(R) H2NNH2 DPIBFdiphenylisobenzofuran O Ph Ph DPPA diphenylphosphoryl azide (diphenylphosphorazidate) P O O O NN+N- Dppb (ddpb) 1,4-bis(diphenylphosphino)butane Ph2P PPh2 dppe 1,2-bis(diphenylphosphino)ethane PPh2 Ph2P dppf1,1-bis(diphenylphosphino)ferrocene Fe PPh2 PPh2 dppmbis(diphenylphosphino)methane Ph2PPPh2 dppp 1,3-bis(diphenylphosphino)propane Ph2PPPh2 DPS (also TBDPS or BPS) t-butyldiphenylsilyl Si TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxviii Abbreviation Chemical Name Chemical Structure DPTCO,O-di(2-pyridyl)thiocarbonate S OONN drdiastereomeric ratio NA DTBAD (DBAD) di-tert-butyl azodicarboxylate N NO O O O DTBB4,4-di-tert-butylbiphenyl DTBP2,6-di-tert-butylpyridine N DTBMP2,6-di-tert-butyl-4-methylpyridine N DTE1,4-dithioerythritol SH OH OH SH DVS1,3-divinyl-1,1,3,3-tetramethyldisiloxane Si O Si Me Me Me Me E+electrophile (denotes any electrophile in general) NA E2bimolecular elimination NA EDeffective dosage NA EDA ethyl diazoacetate O O N+ N- EDDA ethylenediamine diacetate NH3 H3N OAc OAc EDC (EDAC) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (ethyldimethylaminopropylcarbodiimide) N C N N EDCI1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride N C NNH Cl EDCP2,3-bis-phosphonopentanedioic acid (ethylene dicarboxylic 2,3-diphosphonic acid) HOOCCOOH PO3H2 PO3H2 EDGelectron-donating group NA EDTA ethylenediamine tetraacetic acid N N COOH HOOCHOOC COOH TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxix Abbreviation Chemical Name Chemical Structure eeenantiomeric excess NA EE ethoxyethyl O Eiintramolecular syn elimination NA en ethylenediamine H2N NH2 EOMethoxymethyl O ESRelectron spin resonance (spectroscopy) NA Etethyl ETSA ethyl trimethylsilylacetate O O Si EVEethyl vinyl ether O EWGelectron-withdrawing group NA Fc ferrocenyl Fe FDPfructose-1,6-diphosphate CH2OPO3H2 OH H H2O3POH2C HO H HHO O FDPPpentafluorophenyl diphenylphosphinate PO O Ph Ph F F F F F Flfluorenyl FMOfrontier molecular orbital (theory) NA Fmoc 9-fluorenylmethoxycarbonyl O O fod6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5- octanedione O O F F F F F F F fpflash point NA FSMMesoporous silica NA FTT1-fluoro-2,4,6-trimethylpyridinium triflate NFS O O O F F F TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxx Abbreviation Chemical Name Chemical Structure FVPflash vacuum pyrolysis NA GEBCgel entrapped base catalyst NA hhours (length of reaction time) NA h irradiation with light NA HATU O-(7-azabenzotriazol-1-yl)-N,N,N,N- tetramethyluronium hexafluorophosphate N N O+ N N N N PF6 Hetheterocycle NA hfacac hexafluoroacetylacetone F3C OO CF3 HFIP1,1,1,3,3,3-hexafluoro-2-propanol (hexafluoroisopropanol) OH F F FF F F HGK4-hydroxy-2-ketoglutarate O OO O O HO Hgmmmillimeter of mercury (760 Hgmm = 1 atm = 760 Torr) NA HLEhorse liver esterase NA Hmb2-hydroxy-4-methoxybenzyl OOH HMDS1,1,1,3,3,3-hexamethyldisilazane Si H N Si HMPA hexamethylphosphoric acid triamide (hexamethylphosphoramide) P O N N N HMPThexamethylphosphorous triamide PN N N HOAt 1-hydroxy-7-azabenzotriazole N N N N OH HOBt (HOBT) 1-hydroxybenzotriazole N N N OH HOMOhighest occupied molecular orbital NA HOSuN-hydroxysuccinimide OO N OH HPLChigh-pressure liquid chromatography NA HWEHorner-Wadsworth-Emmons NA iiso NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxi Abbreviation Chemical Name Chemical Structure IBA 2-iodosobenzoic acid O HO I O IBXo-iodoxybenzoic acid I O O O HO IDCPbis(2,4,6-collidine)iodonium perchlorate NI+NClO4- Imid (Im) imidazole N HN INOCintramolecular nitrile oxide cycloaddition NA IPA isopropyl alcohol HO Ipcisopinocamphenyl H IRinfrared spectroscopy NA K-10a type of Montmorillonite clay NA KDA potassium diisopropylamide K N KHMDSpotassium bis(trimethylsilyl)amide K N SiSi KSFa type of Montmorillonite clay NA Lligand NA L.R. Lawessons reagent (2,4-bis-(4-methoxyphenyl)- 1,3,2,4dithiadiphosphetane 2,4-dithion) S PS P S S OMe MeO LA Lewis acid NA LAB lithium amidotrihydroborate LiH2NBH3 LAH lithium aluminum hydride LiAlH4 LD50dose that is lethal to 50% of the test subjects (cells, animals, humans etc.) NA LDA lithium diisopropylamide Li N LDBBlithium 4,4-t-butylbiphenylide Li TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxii Abbreviation Chemical Name Chemical Structure LDElithium diethylamide Li N LDPElithium perchlorate-diethyl etherate LiClO4 - Et2O LHMDS (LiHMDS) lithium bis(trimethylsilyl)amide Li N SiSi LICA lithium isopropylcyclohexylamide Li N LICKOR (super base) butyllithium-potassium tert-butoxide BuLi - KOt-Bu liq.liquid NA LiTMP (LTMP) lithium 2,2,6,6-tetramethylpiperidide N Li LPTlithium pyrrolidotrihydroborate (lithium pyrrolidide-borane) Li(CH2)4NBH3 L-selectride lithium tri-sec-butylborohydride Li BH LTA lead tetraacetate Pb(OAc)4 LUMOlowest unoccupied molecular orbital NA lut2,6-lutidine N mmeta NA MA maleic anhydride O O O MAD methyl aluminum bis(2,6-di-t-butyl-4- methylphenoxide) OAlMe 2 MAT methyl aluminum bis(2,4,6-tri-t-butylphenoxide) OAlMe 2 TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxiii Abbreviation Chemical Name Chemical Structure MBT2-mercaptobenzothiazole S N HS m-CPBA meta chloroperbenzoic acid Cl COOOH Memethyl CH3 MEM(2-methoxyethoxy)methyl O O MEPYmethyl 2-pyrrolidone-5(S)-carboxylate H N O O O Mesmesityl mesal N-methylsalicylaldimine HO N MICmethyl isocyanate NCO MMPP (MMPT) magnesium monoperoxyphthalate Mg2+ O O O O O MOMmethoxymethyl O MoOPH oxodiperoxomolybdenum(pyridine)- (hexamethylphosphoric triamide) NA mpmelting point NA MPamegapascal = 106 Pa = 10 atm (pressure) MPD (NMP) N-methyl-2-pyrrolidinone N O MPMmethoxy(phenylthio)methyl S O MPM (PMB) p-methoxybenzyl O TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxiv Abbreviation Chemical Name Chemical Structure MPPCN-methyl piperidinium chlorochromate OCr O O Cl NH Msmesyl (methanesulfonyl) S O O CH3 MSmass spectrometry NA MSmolecular sieves NA MSA methanesulfonic acid S O O CH3HO MSHo-mesitylenesulfonyl hydroxylamine H N HOS O O MSTFA N-methyl-N-(trimethylsilyl) trifluoroacetamide O N F F F Si MTAD N-methyltriazolinedione N NN O O MTEE (MTBE) methyl t-butyl ether O MTMmethylthiomethyl S MTOmethyltrioxorhenium Re O O O CH3 Mtr(4-methoxy-2,3,6-trimethylphenyl)sulfonyl OMe MeMe Me S O O MVKmethyl vinyl ketone O mw microwave NA nnormal (e.g. unbranched alkyl chain) NA NADPH nicotinamide adenine dinucleotide phosphate N HH NH2 O O OHOH O O OOH O P O OH OH N NN N NH2 P O OH OP O OH TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxv Abbreviation Chemical Name Chemical Structure NaHMDSsodium bis(trimethylsilyl)amide Na N SiSi Naph (Np) naphthyl NBA N-bromoacetamide O N H Br NBD (nbd) norbornadiene NBSN-bromosuccinimide O O NBr NCSN-chlorosuccinimide O O NCl Nfnonafluorobutanesulfonyl S O O FF FF F F F F F NHPIN-hydroxyphthalimide O O NOH NISN-iodosuccinimide OO N I NMMN-methylmorpholine NO NMON-methylmorpholine oxide NO O NMPN-methyl-2-pyrrolidinone N O NMRnuclear magnetic resonance NA NORPHOSbis(diphenylphosphino)bicyclo2.2.1-hept-5-ene Ph2P PPh2 Nos4-nitrobenzenesulfonyl S O O N O O TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxvi Abbreviation Chemical Name Chemical Structure NPMN-phenylmaleimide O O N NRno reaction NA Ns2-nitrobenzenesulfonyl S O O NO O NSAID non steroidal anti-inflammatory drug NA Nucnucleophile (general) NA oortho NA Oxone potassium peroxymonosulfate KHSO5 ppara NA PAP 2,8,9-trialkyl-2,5,8,9-tetraaza- 1-phospha-bicyclo3.3.3undecane P N N N N R R R PBPpyridinium bromide perbromide N H Br3 PCCpyridinium chlorochromate N H O Cr O O Cl PDCpyridinium dichromate N H Cr O O O O Cr O O ON H PEGpolyethylene glycol NA Pf9-phenylfluorenyl Ph pfbperfluorobutyrate O O F F FF F F F Phphenyl PHAL phthalazine N N phen 9,10-phenanthroline NN TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxvii Abbreviation Chemical Name Chemical Structure Phthphthaloyl C C O O pic 2-pyridinecarboxylate NO O PIDA (BAIB or DIB) phenyliodonium diacetate I O O O O PIFA phenyliodonium bis(trifluoroacetate) I O O F3C O O CF3 Piv pivaloyl O PLEpig liver esterase NA PMB (MPM) p-methoxybenzyl O PMP4-methoxyphenyl O PMP1,2,2,6,6-pentamethylpiperidine N Me Me Me Me Me PNBp-nitrobenzyl N O O PNZp-nitrobenzyloxycarbonyl O O N O O PPA polyphosphoric acid NA PPI2-phenyl-2-(2-pyridyl)-2H-imidazole N N N PPLpig pancreatic lipase NA PPO4-(3-phenylpropyl)pyridine-N-oxide NPhO PPSEpolyphosphoric acid trimethylsilyl ester NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxviii Abbreviation Chemical Name Chemical Structure PPTSpyridinium p-toluenesulfonate N H S O O O Prpropyl psi pounds per square inch NA PT1-phenyl-1H-tetrazol-yl N N N N Ph P.T.proton transfer NA PTAB phenyltrimethylammonium perbromide N Br3 PTCPhase transfer catalyst NA PTMSE(2-phenyl-2-trimethylsilyl)ethyl Si PTSA (or TsOH) p-toluenesulfonic acid CH3HO3S PVPpoly(4-vinylpyridine) NA Py (pyr) pyridine N r.t.room temperature NA racracemic NA RAMP (R)-1-amino-2-(methoxymethyl)pyrrolidine N (R) O NH2 RaNiRaney nickel NA RBRose Bengal See Rose bengal RCAM ring-closing alkyne metathesis NA RCMring-closing metathesis NA Rds (or RDS) rate-determining step NA Red-Al sodium bis(2-methoxyethoxy) aluminum hydride AlO O O O H H Na Rhamrhamnosyl O O H O H Me O H Rfperfluoroalkyl group CnF2n+1 Rfretention factor in chromatography NA ROMring-opening metathesis NA ROMPring-opening metathesis polymerization NA TABLE OF CONTENTSTABLE OF CONTENTSSEARCH TEXTSEARCH TEXT xxxix Abbreviation Chemical Name Chemical Structure Rose Bengal (RB) 2,4,5,7-tetraiodo-3,4,5,6-tetrachlorofluorescein disodium salt (a photosensitizer) O I O II O I Cl Cl Cl Cl COO 2 Na sseconds (length of reaction time) NA S,S,-chiraphos (S,S)-2,3-bis(diphenylphosphino)butane (S) (S) PPh2 PPh2 SalenN,N-ethylenebis(salicylideneiminato) bis(salicylidene)ethylenediamine NN OHHO salophen o-phenylenebis(salicylideneiminato) NN OHHO SAMP (S)-1-amino-2-(methoxymethyl)pyrrolidine N O NH2 SC CO2supercritical carbon-dioxide NA SDSsodium dodecylsulfate Na SOO O O secsecondary NA SEM2-(trimethylsilyl)ethoxymethyl O Si SES2-(trimethylsilyl)ethylsulfonyl Si S O O SETsingle electron transfer NA Sia1,2-dimethylpropyl (secondary isoamyl) SPBsodium perborate Na BO3