SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY LACTONES BY SHARPLESS ASYMMETRIC DIHYDROXYLATIONS OF KETENE ACETALS, ENOL ETHERS, AND ENE LACTONES

被引：36

作者：

CURRAN, DP

KO, SB

机构：

[1] Department of Chemistry, University of Pittsburgh, Pittsburgh

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 21期

关键词：

D O I：

10.1021/jo00100a005

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three different AD routes to optically active alpha-hydroxy lactones of good to excellent optical purity are reported. The substrates for the AD reaction are endocyclic ketene acetals, endocyclic enol ethers, and exocyclic alpha,beta-unsaturated lactones.

引用

页码：6139 / 6141

页数：3

共 50 条

[31] STEREOSELECTIVE REACTIONS .5. DESIGN OF THE ASYMMETRIC-SYNTHESIS OF LIGNAN LACTONES - SYNTHESIS OF OPTICALLY-ACTIVE PODORHIZON AND DEOXYPODORHIZON BY 1,3-ASYMMETRIC INDUCTION
TOMIOKA, K
MIZUGUCHI, H
KOGA, K
CHEMICAL & PHARMACEUTICAL BULLETIN, 1982, 30 (12) : 4304 - 4313
[32] Enzymatic Synthesis of Optically Active Lactones via Asymmetric Bioreduction using Ene-Reductases from the Old Yellow Enzyme Family
Turrini, Nikolaus G.
Hall, Melanie
Faber, Kurt
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (08) : 1861 - 1871
[33] Synthesis and Antifeedant Activity of Racemic and Optically Active Hydroxy Lactones with the p-Menthane System
Grudniewska, Aleksandra
Klobucki, Marek
Dancewicz, Katarzyna
Szczepanik, Maryla
Gabrys, Beata
Wawrzenczyk, Czeslaw
PLOS ONE, 2015, 10 (07):
[34] PREPARATIVE BIO-ORGANIC CHEMISTRY .1. SYNTHESIS OF OPTICALLY-ACTIVE ALKYNYL ALCOHOLS AND ALPHA-HYDROXY ESTERS BY MICROBIAL ASYMMETRIC HYDROLYSIS OF THE CORRESPONDING ACETATES
MORI, K
AKAO, H
TETRAHEDRON, 1980, 36 (01) : 91 - 96
[35] ASYMMETRIC HYDROGENOLYSIS OF HYDRAZONES - SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-ALANINE
KIYOOKA, S
TAKESHIMA, K
YAMAMOTO, H
SUZUKI, K
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1976, 49 (07) : 1897 - 1900
[36] BIFUNCTIONAL CHIRAL SYNTHONS VIA MICROBIOLOGICAL METHODS .2. OPTICALLY-ACTIVE ALPHA-HYDROXY ALDEHYDES
TAKAISHI, Y
YANG, YL
DITULLIO, D
SIH, CJ
TETRAHEDRON LETTERS, 1982, 23 (52) : 5489 - 5492
[37] OXYGENATION OF SILYL ENOL ETHERS AND SILYL KETENE ACETALS WITH MOLECULAR-OXYGEN AND ALDEHYDE CATALYZED BY NICKEL(II) COMPLEX - A CONVENIENT METHOD FOR THE PREPARATION OF ALPHA-HYDROXY CARBONYL-COMPOUNDS
TAKAI, T
YAMADA, T
RHODE, O
MUKAIYAMA, T
CHEMISTRY LETTERS, 1991, (02) : 281 - 284
[38] SYNTHESIS OF BIS-GAMMA-LACTONES FROM DIACETONE GLUCOSE .5. OPTICALLY-ACTIVE CANADENSOLIDE
ANDERSON, RC
FRASERREID, B
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (24): : 4786 - 4790
[39] ASYMMETRIC REDUCTION OF CARBONYL-COMPOUNDS BY YEAST .2. PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY AND BETA-HYDROXY CARBOXYLIC-ACID DERIVATIVES
DEOL, BS
RIDLEY, DD
SIMPSON, GW
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (11) : 2459 - 2467
[40] SYNTHESIS OF OPTICALLY ACTIVE ALPHA-HYDROXY ACIDS BY ADDITION OF ORGANOZINE COMPOUNDS TO (-)MENTHYL PHENYLGLYOXALATE
BOIREAU, G
DEBERLY, A
ABENHAIM, D
TETRAHEDRON, 1989, 45 (18) : 5837 - 5844

← 1 2 3 4 5 →