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

[1] SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS
BOIREAU, G
ABENHAIM, D
DEBERLY, A
SABOURAULT, B
TETRAHEDRON LETTERS, 1982, 23 (12) : 1259 - 1262
[2] Synthesis of optically active butenolides and γ-lactones by the sharpless asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters
Harcken, C
Brückner, R
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) : 2750 - 2752
[3] APPLICATIONS OF OPTICALLY-ACTIVE ARYL CYANOHYDRINS IN THE SYNTHESIS OF ALPHA-HYDROXY ALDEHYDES, ALPHA-HYDROXY KETONES AND BETA-HYDROXY AMINES
JACKSON, WR
JACOBS, HA
JAYATILAKE, GS
MATTHEWS, BR
WATSON, KG
AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (12) : 2045 - 2062
[4] PREPARATION OF OPTICALLY-ACTIVE ALPHA-HYDROXY KETONE DERIVATIVES BY ENZYME-MEDIATED HYDROLYSIS OF ENOL ESTERS
MATSUMOTO, K
SUZUKI, N
OHTA, H
TETRAHEDRON LETTERS, 1990, 31 (49) : 7159 - 7162
[5] Synthesis of optically active α-hydroxy carbonyl compounds by the catalytic, enantioselective oxidation of silyl enol ethers and ketene acetals with (salen)manganese(III) complexes
Adam, W
Fell, RT
Stegmann, VR
Saha-Möller, CR
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (04) : 708 - 714
[6] Synthesis of optically active alpha-hydroxycarbonyl compounds by (Salen)Mn(III)-catalyzed oxidation of silyl enol ethers and silyl ketene acetals
Adam, W
Fell, RT
MockKnoblauch, C
SahaMoller, CR
TETRAHEDRON LETTERS, 1996, 37 (36) : 6531 - 6534
[7] CHROMIUM(III) COMPLEXES WITH SOME OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS
ELSHAHAWI, MS
ELBINDARY, AA
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1993, 48 (03): : 282 - 286
[8] SYNTHESIS OF OPTICALLY-ACTIVE 4-ALKYL GAMMA-LACTONES
VIGNERON, JP
BLOY, V
TETRAHEDRON LETTERS, 1980, 21 (18) : 1735 - 1738
[9] NOVEL SYNTHESIS OF OPTICALLY-ACTIVE LACTONES FROM 4-THIANONE
MATSUYAMA, H
FUJII, S
KAMIGATA, N
HETEROCYCLES, 1991, 32 (10) : 1875 - 1878
[10] ASYMMETRIC HALOLACTONIZATION REACTION - HIGHLY EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE ALPHA-HYDROXY ACIDS FROM ALPHA,BETA-UNSATURATED ACIDS
TERASHIMA, S
JEW, S
TETRAHEDRON LETTERS, 1977, (11) : 1005 - 1008

← 1 2 3 4 5 →