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 [J].

BERNARDI, A ;

CAPELLI, AM ;

COMOTTI, A ;

GENNARI, C ;

GARDNER, M ;

GOODMAN, JM ;

PATERSON, I .

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 [J].

BROWN, HC ;

DHAR, RK ;

GANESAN, K ;

SINGARAM, B .

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 [J].

BROWN, HC ;

DHAR, RK ;

BAKSHI, RK ;

PANDIARAJAN, PK ;

SINGARAM, B .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (09) :3441-3442

← 1 2 3 4 5 →