GENERAL-METHOD TO TRANSFORM CHIRAL 2,3-EPOXYALCOHOLS INTO ERYTHRO OR THREO 1,2-EPOXYALCOHOLS WITH TOTAL STEREOCHEMICAL CONTROL

被引:30
作者
PALAZON, JM [1 ]
ANORBE, B [1 ]
MARTIN, VS [1 ]
机构
[1] UNIV LA LAGUNA,INST QUIM ORGAN,LA LAGUNA,SPAIN
关键词
D O I
10.1016/S0040-4039(00)85114-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:4987 / 4990
页数:4
相关论文
共 10 条
[1]   SELECTIVE TRANSFORMATION OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-1 [J].
BEHRENS, CH ;
KO, SY ;
SHARPLESS, KB ;
WALKER, FJ .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) :5687-5696
[2]   TI(O-I-PR)4-MEDIATED NUCLEOPHILIC OPENINGS OF 2,3-EPOXY ALCOHOLS - A MILD PROCEDURE FOR REGIOSELECTIVE RING-OPENING [J].
CARON, M ;
SHARPLESS, KB .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1557-1560
[3]   CHIRAL REAGENTS FROM TARTARIC ACID - 1-BENZYLOXY-3,4-EPOXY-2-BUTANOL, A VERSATILE INTERMEDIATE FOR THE SYNTHESIS OF ENANTIOMERS [J].
HUNGERBUHLER, E ;
SEEBACH, D ;
WASMUTH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1979, 18 (12) :958-960
[4]   THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].
KATSUKI, T ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976
[5]   SYNTHESIS OF SACCHARIDES AND RELATED POLYHYDROXYLATED NATURAL-PRODUCTS .3. EFFICIENT CONVERSION OF 2,3-ERYTHRO-ALDOSES TO 2,3-THREO-ALDOSES [J].
LEE, AWM ;
MARTIN, VS ;
MASAMUNE, S ;
SHARPLESS, KB ;
WALKER, FJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (12) :3515-3516
[6]   KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].
MARTIN, VS ;
WOODARD, SS ;
KATSUKI, T ;
YAMADA, Y ;
IKEDA, M ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240
[7]   THE USE OF DIETHYL AZODICARBOXYLATE AND TRIPHENYLPHOSPHINE IN SYNTHESIS AND TRANSFORMATION OF NATURAL-PRODUCTS [J].
MITSUNOBU, O .
SYNTHESIS-STUTTGART, 1981, (01) :1-28
[8]   EPOXY ALCOHOL REARRANGEMENTS - HYDROXYL-MEDIATED DELIVERY OF LEWIS ACID PROMOTERS [J].
MORGANS, DJ ;
SHARPLESS, KB ;
TRAYNOR, SG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (02) :462-464
[9]   TOTAL SYNTHESIS OF CARBOHYDRATES .2. REGIOCHEMICAL CONTROL OF NUCLEOPHILIC RING-OPENING OF ACYLATED 2,3-EPOXY ALCOHOLS [J].
ROUSH, WR ;
BROWN, RJ ;
DIMARE, M .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (25) :5083-5093
[10]   STEREO AND REGIOSELECTIVE OPENINGS OF CHIRAL 2,3-EPOXY ALCOHOLS - VERSATILE ROUTES TO OPTICALLY PURE NATURAL-PRODUCTS AND DRUGS - UNUSUAL KINETIC RESOLUTIONS [J].
SHARPLESS, KB ;
BEHRENS, CH ;
KATSUKI, T ;
LEE, AWM ;
MARTIN, VS ;
TAKATANI, M ;
VITI, SM ;
WALKER, FJ ;
WOODARD, SS .
PURE AND APPLIED CHEMISTRY, 1983, 55 (04) :589-604