Stereoselective synthesis of syn-α-methyl-β-hydroxy esters

被引：9

作者：

Carda, M ^{[1
]}

Murga, J

Falomir, E

González, F

Marco, JA

机构：

[1] Univ Jaume 1, Dept Quim Inorgan & Organ, E-12080 Castellon de La Plana, Spain

[2] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Valencia, Spain

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(00)00274-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Boron enolates of an ethyl ketone structurally related to erythrulose react with achiral aldehydes in a highly stereoselective fashion to yield 1,2-sqn/1,3-syn stereoisomers. Oxidative cleavage of the aldol adducts yields enantiopure O-formylated syn-alpha-methyl-beta-hydroxy esters, easily cleaved to the corresponding hydroxyl-free compounds. The aforementioned ketone behaves therefore as a chiral propionate enolate equivalent. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：3211 / 3220

页数：10

共 49 条

[1] [Anonymous], 1984, ASYMMETRIC SYNTHESIS
[2] [Anonymous], [No title captured]
[3] [Anonymous], 1994, Aldrichimica Acta
[4] [Anonymous], 1997, ORG REACT
[5] BEAU JM, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P135
[6] ORIGINS OF STEREOSELECTIVITY IN CHIRAL BORON ENOLATE ALDOL REACTIONS - A COMPUTATIONAL STUDY USING TRANSITION-STATE MODELING
BERNARDI, A
CAPELLI, AM
COMOTTI, A
GENNARI, C
GARDNER, M
GOODMAN, JM
PATERSON, I
[J]. TETRAHEDRON, 1991, 47 (20-21) : 3471 - 3484
[7] BLIZZARD T, 1990, RECENT PROGRESS IN THE CHEMICAL SYNTHESIS OF ANTIBIOTICS, P65
[8] BRAUN M, 1996, HOUBENWEYLS METHODS, V3, P1603
[9] ENOLBORATION .2. DICYCLOHEXYLCHLOROBORANE TRIETHYLAMINE AS A CONVENIENT REAGENT FOR REGIOSELECTIVE AND STEREOSELECTIVE ENOLBORATION OF REPRESENTATIVE CLASSES OF KETONES
BROWN, HC
DHAR, RK
GANESAN, K
SINGARAM, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) : 2716 - 2721
[10] MAJOR EFFECT OF THE LEAVING GROUP IN DIALKYLBORON CHLORIDES AND TRIFLATES IN CONTROLLING THE STEREOSPECIFIC CONVERSION OF KETONES INTO EITHER (E)-ENOL OR (Z)-ENOL BORINATES
BROWN, HC
DHAR, RK
BAKSHI, RK
PANDIARAJAN, PK
SINGARAM, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) : 3441 - 3442

← 1 2 3 4 5 →