PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-HYDROXY ACID-DERIVATIVES FROM ALPHA-ALKOXYORGANOSTANNANES

被引:57
作者
CHAN, PCM [1 ]
CHONG, JM [1 ]
机构
[1] UNIV WATERLOO,GUELPH WATERLOO CTR GRAD WORK CHEM,DEPT CHEM,WATERLOO N2L 3G1,ONTARIO,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4039(00)88895-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically enriched (95-98%) α-alkoxy acids of defined absolute stereochemistry were prepared in good (83-99%) yields from α-alkoxyorganostannanes. © 1990.
引用
收藏
页码:1985 / 1988
页数:4
相关论文
共 15 条
[1]   ASYMMETRIC REDUCTION OF ACYLSTANNANES - PREPARATION OF ENANTIOMERICALLY ENRICHED ALPHA-ALKOXYSTANNANES [J].
CHAN, PCM ;
CHONG, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (23) :5584-5586
[2]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[3]  
HANESSIAN S, 1983, TOTAL SYNTHESIS NATU, pCH2
[4]   AMELIORATION OF THE CONJUGATE ADDITION CHEMISTRY OF ALPHA-ALKOXYCOPPER REAGENTS - APPLICATION TO THE STEREOSPECIFIC SYNTHESIS OF C-GLYCOSIDES [J].
HUTCHINSON, DK ;
FUCHS, PL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (16) :4930-4939
[5]   RESOLUTION OF BINAPHTHOLS AND SPIROBIINDANOLS USING CHOLESTEROL ESTERASE [J].
KAZLAUSKAS, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :4953-4959
[6]   COPPER (I)-PROMOTED CONDENSATION OF ALPHA-AMINO-ACIDS WITH BETA-KETO THIO ESTERS - SYNTHESIS OF N-ACYLATED L-LEUCINE DERIVATIVES CONTAINING (S)-4-HYDROXY-5-METHYL-3-OXOHEXANOIC AND (S)-4-HYDROXY-2,5-DIMETHYL-3-OXOHEXANOIC ACID [J].
KIM, HO ;
OLSEN, RK ;
CHOI, OS .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (20) :4531-4536
[7]   L-LACTATE DEHYDROGENASE - SUBSTRATE-SPECIFICITY AND USE AS A CATALYST IN THE SYNTHESIS OF HOMOCHIRAL 2-HYDROXY ACIDS [J].
KIM, MJ ;
WHITESIDES, GM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2959-2964
[8]   PREPARATION OF OPTICALLY-ACTIVE 2-FURYLCARBINOLS BY KINETIC RESOLUTION USING THE SHARPLESS REAGENT AND THEIR APPLICATION IN ORGANIC-SYNTHESIS [J].
KUSAKABE, M ;
KITANO, Y ;
KOBAYASHI, Y ;
SATO, F .
JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (09) :2085-2091
[9]   EASY AND GENERAL-METHOD TO SYNTHESIZE CHIRAL 2-HYDROXYACID BENZOATES [J].
MARTIN, VS ;
NUNEZ, MT ;
TONN, CE .
TETRAHEDRON LETTERS, 1988, 29 (22) :2701-2702
[10]   A STEREOSPECIFIC CONVERGENT COUPLING OF NUCLEOPHILIC AND ELECTROPHILIC CHIRAL CARBONS [J].
MATTESON, DS ;
TRIPATHY, PB ;
SARKAR, A ;
SADHU, KM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4399-4402