Chemocontrolled reduction of α-keto esters by hydrides:: a possible solution for selective reduction of the ester function

被引：8

作者：

Dalla, V ^{[1
]}

Catteau, JP ^{[1
]}

机构：

[1] Univ Lille 1, Chim Organ Phys Lab, CNRS, URA 351, F-59655 Villeneuve Dascq, France

来源：

TETRAHEDRON | 1999年 / 55卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(99)00317-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha- keto primary alcohols or alpha-silyloxy ketones have been obtained with a high level of selectivity from enolic a-keto esters in two steps, with the reduction of the alpha-silyloxy alpha,beta-unsaturated ester by LiAlH4 as the key step. The methodology developed in this work represents a "reversed" chemoselective reduction of the ester group instead of the keto of an enolic alpha-keto ester due to a one-pot sequential ester reduction-desilylation or silyl migration process. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：6497 / 6510

页数：14

共 23 条

[1] The role of monomer in alkylation reactions of the lithium enolate of p-phenylisobutyrophenone in tetrahydrofuran [J].

Abbotto, A ;

Leung, SSW ;

Streitwieser, A ;

Kilway, KV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :10807-10813

[2] A general and straightforward approach to alpha,omega-ketoesters [J].

Babudri, F ;

Fiandanese, V ;

Marchese, G ;

Punzi, A .

TETRAHEDRON, 1996, 52 (42) :13513-13520

[3] ENOLATE ANIONS AS PROTECTING GROUPS FOR KETONES DURING REDUCTION BY HYDRIDE [J].

BARTON, DHR ;

HESSE, RH ;

WILSHIRE, C ;

PECHET, MM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (09) :1075-1080

[4] CARBANION OR ENOLATE - A H-1, C-13, AND SI-29 NMR SPECTROSCOPIC ANALYSIS [J].

BAUDRILLARD, V ;

PLE, G ;

DAVOUST, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1473-1474

[5] REDUCTIVE CLEAVAGE OF TERT-BUTYLDIMETHYLSILYL ETHERS BY DIISOBUTYLALUMINUM HYDRIDE [J].

COREY, EJ ;

JONES, GB .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (03) :1028-1029

[6] Chemocontrolled reduction of aromatic alpha-ketoesters by NaBH4: Selective synthesis of alpha-hydroxy esters or 1,2-diols [J].

Dalla, V ;

Cotelle, P ;

Catteau, JP .

TETRAHEDRON LETTERS, 1997, 38 (09) :1577-1580

[7]

DELAHERAS MA, 1997, J ORG CHEM, V62, P8620

[8] Electrophilic alpha-p-tolylhydrazonylation of tert-butyl alkanoates and tertiary alkanamides with tert-butyl p-tolylazo sulfide [J].

DellErba, C ;

Novi, M ;

Petrillo, G ;

Tavani, C .

TETRAHEDRON, 1996, 52 (16) :5889-5898

[9] Nonionic superbase-catalyzed silylation of alcohols [J].

DSa, BA ;

McLeod, D ;

Verkade, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (15) :5057-5061

[10] Carboxylic acids and esters [J].

Franklin, AS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2451-2465

← 1 2 3 →