TABLE OF CONTENTS SEARCH TEXT V. LIST OF ABBREVIATIONS Abbreviation Chemical Name Chemical Structure O O O 18-Cr-6 18-crown-6 O O O O Ac acetyl acac acetylacetonyl O O AA asymmetric aminohydroxylation NA AD asymmetric dihydroxylation NA ad adamantyl O N ADDP 1,1'-(azodicarbonyl)dipiperidine NN N O ADMET acyclic diene metathesis polymerization NA O N acaen N,N’-bis(1-methyl-3-oxobutylidene)ethylenediamine N O AIBN 2,2'-azo bisisobutyronitrile N NN N Alloc allyloxycarbonyl O O Am amyl (n-pentyl) An p-anisyl O ANRORC anionic ring-opening ring-closing NA aq aqueous NA O AQN anthraquinone O Ar aryl (substituted aromatic ring) NA xvii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure ATD aluminum tris(2,6-di-tert-butyl-4-methylphenoxide) Al O 3 atm 1 atmosphere = 105 Pa (pressure) NA Ph Al O ATPH aluminum tris(2,6-diphenylphenoxide) Ph 3 BBN (9-BBN) 9-borabicyclo[3.3.1]nonane (9-BBN) B H B 9-borabicyclo[3.3.1]nonyl B BCME bis(chloromethyl)ether ClO Cl O N O BCN N -benzyloxycarbonyloxy-5-norbornene-2,3- O dicarboximide O O Ph P PPh BDPP (2R, 4R) or (2S, 4S) bis(diphenylphosphino)pentane 2 2 (R) (R) BER borohydride exchange resin NA OH BHT 2,6-di-t-butyl-p-cresol (butylated hydroxytoluene) BICP R R bis R R (R) (R) 2( )-2’( )- (dipenylphosphino)-1( ),1’( )- (R) (R) dicyclopentane Ph2P PPh2 O H BINAL-H 2,2'-dihydroxy-1,1'-binaphthyl lithium aluminum Al Li O hydride H BINAP 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl PPh2 PPh2 xviii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure OH BINOL 1,1'-bi-2,2'-naphthol OH O Bip biphenyl-4-sulfonyl S O NN bipy 2,2'-bipyridyl BLA Brönsted acid assisted chiral Lewis acid NA bmin 1-butyl-3-methylimidazolium cation N N H BSMe BMS Borane-dimethyl sulfide complex 3 2 Bn benzyl O BNAH 1-benzyl-1,4-dihydronicotinamide N NH2 BOB 4-benzyloxybutyryl O O Boc t-butoxycarbonyl OO O BOM benzyloxymethyl O Cl O O P BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphinic chloride N N O O bp boiling point NA O O BPD (pinacolato)diboron B B bis O O O O O O Ph BPO benzoyl peroxide Ph BPS (TBDPS) t-butyldiphenylsilyl Si xix TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure BQ benzoquinone OO O Bs brosyl = SBr (4-bromobenzenesulfonyl) O O BSA N,O-bis(trimethylsilyl)acetamide Si NSi BSA Bovine serum albumin NA Bt N 1- or 2-benzotriazolyl N N F BTAF benzyltrimethylammonium fluoride N BTEA benzyltriethylammonium N Cl BTEAC benzyltriethylammonium chloride N O F BTFP 3-bromo-1,1,1-trifluoro-propan-2-one F F Br BTMA benzyltrimethylammonium N BTMSA bis (trimethylsilyl) acetylene Si Si O O SiS Si BTS bis O (trimethylsilyl) sulfate O O S BTSA benzothiazole 2-sulfonic acid HO S O N O Si BTSP bis(trimethylsilyl) peroxide Si O O Bz benzoyl Bu (nBu) n-butyl c cyclo NA xx TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure ca circa NA (approximately) CA O chloroacetyl Cl cerium(IV) ammonium nitrate (cericammonium Ce(NH ) (NO ) CAN nitrate) 4 2 3 6 cat. catalytic NA CB O catecholborane HB O H Ph Ph CBS Corey-Bakshi-Shibata reagent O R = H, alkyl N B R Cbz (Z) benzyloxycarbonyl O O cc. or conc. concentrated NA CCE constant current electrolysis NA O CDI carbonyl diimidazole N N N N CHD 1,3 or 1,4-cyclohexadiene 1,3-CHD 1,4-CHD Ph (S) CHIRAPHOS bis Ph P 2,3- (diphenylphosphino)butane P (S) Ph Ph Chx (Cy) cyclohexyl Cl PF CIP 2-chloro-1,3-dimethylimidazolidinium N NH 6 hexafluorophosphate CM (XMET) cross metathesis NA CMMP cyanomethylenetrimethyl phosphorane P N COD 1,5-cyclooctadiene COT 1,3,5-cyclooctatriene Cp cyclopentadienyl O S O H N CPTS collidinium-p-toluenesulfonate O xxi TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure CRA complex reducing agent NA Cr-PILC chromium-pillared clay catalyst NA CSA camphorsufonic acid O SO3H O CSI chlorosulfonyl isocyanate N S C Cl O O N Br CTAB cetyl trimethylammonium bromide N Cl CTACl cetyl trimethylammonium chloride C15H31 N MnO CTAP cetyl trimethylammonium permanganate 4 C15H31 Δ heat NA d days (length of reaction time) NA N DABCO 1,4-diazabicyclo[2.2.2]octane N N N F DAST diethylaminosulfur trifluoride F SN F DATMP diethylaluminum 2,2,6,6-tetramethylpiperidide N AlEt2 Ph Ph DBA (dba) dibenzylideneacetone O O DBAD di-tert-butylazodicarboxylate N O O N O Br O N O NH DBI dibromoisocyanuric acid N Br O xxii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure O O DBM dibenzoylmethane 2 9 1 N 3 DBN 1,5-diazabicyclo[4.3.0]non-5-ene 8 4 6 7 N 5 DBS dibenzosuberyl 2 11 1 3 10 N DBU 1,8-diazabicyclo[5.4.0]undec-7-ene 4 9 N 7 5 8 6 CN DCA 9,10-dicyanoanthracene CN Cl DCB 1,2-dichlorobenzene Cl N DCC dicyclohexylcarbodiimide C N DCE 1,1-dichloroethane Cl Cl DCM dichloromethane CH2Cl2 CN DCN 1,4-dicyanonaphthalene CN Dcpm dicyclopropylmethyl DCU N,N’-dicyclohexylurea O N N H H O NC Cl DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone NC Cl O de diastereomeric excess NA xxiii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure O N O DEAD diethyl azodicarboxylate O N O DEIPS diethylisopropylsilyl Si O OEt EtO O DEPBT 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin- P N 4(3H)-one O N N O OH (R) O DET (R) diethyl tartrate O HO O DHP 3,4-dihydro-2H-pyran O OMe OH DHQ dihydroquinine H N N H Et Et N N N N H H (DHQ)2PHAL bis(dihydroquinino)phthalazine O O H H MeO OMe N N OMe DHQD dihydroquinidine H N OH H N Et Et N N NN H H O O H H (DHQD)2PHAL bis(dihydroquinidino)phthalazine MeO OMe N N O DIAD NO diisopropyl azodicarboxylate O N O O DIB (diacetoxyiodo)benzene O (BAIB or PIDA) I O O xxiv TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure H DIBAL (DIBAH) diisobutylaluminum hydride DIBAL-H Al N DIC diisopropyl carbodiimide C N O (R) PPh2 diop bis 4,5- -[(diphenylphosphanyl)methyl]-2,2-dimethyl- O (R) PPh [1,3]dioxolane 2 O DIPAMP 1,2-bis(o-anisylphenylphosphino)ethane P P O DIPEA diisopropylethylamine N (Hünig's base) O OH O DIPT (R) (R) diisopropyl tartrate O HO O O C H O DLP 10 21 dilauroyl peroxide O C10H21 O O DMA (DMAC) N,N -dimethylacetamide N O O DMAD dimethyl acetylene dicarboxylate O O DMAP N,N -4-dimethylaminopyridine NN DMB m-dimethoxybenzene OO DMDO dimethyl dioxirane O O O DME 1,2-dimethoxyethane O xxv TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure ON DMF N,N-dimethylformamide H O DMI 1,3-dimethylimidazolidin-2-one N N O DMP Dess-Martin periodinane O I OAc AcO OAc DMPS dimethylphenylsilyl Si 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone N DMPU N O (N,N-dimethyl propylene urea) S Me DMTSF dimethyl(methylthio)sulfonium tetrafluoroborate Me S BF4 Me DMS dimethylsulfide S O DMSO dimethylsulfoxide S DMT 4,4’-dimethoxytrityl OO O N N 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4- O DMTMM methylmorpholinium chloride O N N Cl DMTr 4,4’-dimethyltrityl S O F DMTST (dimethylthio)methylsulfonium S O S F trifluoromethanesulfonate S O F DNA deoxyribonucleic acid NA xxvi TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure DPA (DIPA) diisopropylamine N H DPBP 2,2'-bis(diphenylphosphino)biphenyl (S) Ph2P PPh2 O DPDC OO diisopropyl peroxydicarbonate O O O N- N+ DPDM diphenyl diazomethane H2N NH2 DPEDA 1,2-diamino-1,2-diphenylethane (R) (R) Ph DPIBF diphenylisobenzofuran O Ph DPPA diphenylphosphoryl azide (diphenylphosphorazidate) O O P O NN+ N- Dppb (ddpb) 1,4-bis(diphenylphosphino)butane Ph2P PPh2 PPh dppe 1,2-bis(diphenylphosphino)ethane 2 Ph2P PPh2 dppf 1,1'-bis(diphenylphosphino)ferrocene Fe PPh2 Ph P PPh dppm bis(diphenylphosphino)methane 2 2 Ph PPPh dppp 1,3-bis(diphenylphosphino)propane 2 2 DPS (also TBDPS or t-butyldiphenylsilyl BPS) Si xxvii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure S DPTC O,O’-di(2’-pyridyl)thiocarbonate N O O N dr diastereomeric ratio NA O DTBAD (DBAD) di-tert -butyl azodicarboxylate N O O N O DTBB 4,4’-di-tert-butylbiphenyl DTBP 2,6-di-tert-butylpyridine N DTBMP 2,6-di-tert-butyl-4-methylpyridine N OH DTE 1,4-dithioerythritol SH SH OH Me Me DVS 1,3-divinyl-1,1,3,3-tetramethyldisiloxane O Si Si Me Me + E electrophile (denotes any electrophile in general) NA E2 bimolecular elimination NA ED effective dosage NA O EDA ethyl diazoacetate N- N+ O EDDA ethylenediamine diacetate H N OAc 3 NH OAc 3 EDC (EDAC) 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (ethyldimethylaminopropylcarbodiimide) N N C N EDCI 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide NNHCl C hydrochloride N PO3H2 EDCP 2,3-bis-phosphonopentanedioic acid HOOC COOH (ethylene dicarboxylic 2,3-diphosphonic acid) PO3H2 EDG electron-donating group NA HOOC HOOC EDTA N ethylenediamine tetraacetic acid N COOH COOH xxviii TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure ee enantiomeric excess NA ethoxyethyl EE O Ei intramolecular syn elimination NA H N en 2 ethylenediamine NH2 EOM ethoxymethyl O ESR electron spin resonance (spectroscopy) NA Et ethyl O ETSA ethyl trimethylsilylacetate Si O EVE ethyl vinyl ether O EWG electron-withdrawing group NA Fc ferrocenyl Fe H O POH C 2 3 2 O OH H HO FDP fructose-1,6-diphosphate H CH2OPO3H2 HO H F F F FDPP pentafluorophenyl diphenylphosphinate O F Ph POF Ph Fl fluorenyl FMO frontier molecular orbital (theory) NA O O Fmoc 9-fluorenylmethoxycarbonyl F F F O O fod 6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5- F octanedione F F F fp flash point NA FSM Mesoporous silica NA O F FTT 1-fluoro-2,4,6-trimethylpyridinium triflate NFO S F O F xxix TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure FVP flash vacuum pyrolysis NA GEBC gel entrapped base catalyst NA h hours (length of reaction time) NA