Asymmetric methoxyselenenylation of alkyl vinyl ethers: a new route to chiral acetals

被引：20

作者：

Uchiyama, M ^{[1
]}

Satoh, S ^{[1
]}

Ohta, A ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Tokyo 1920392, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 08期

关键词：

chiral selenium compounds; asymmetric methoxyselenenylation; vinyl ethers; chiral acetals;

D O I：

10.1016/S0040-4039(00)02285-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric methoxyselenenylation of alkyl vinyl ethers afforded the corresponding chiral acetals with moderate to good diastereoselectivity. This reaction and subsequent deselenenylation provided a new method of preparing enantiomerically enriched acetals in which the acetal carbon was the only stereogenic center. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1559 / 1562

页数：4

共 40 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].

ALEXAKIS, A ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511

[2]

Back T. G., 1987, ORGANOSELENIUM CHEM

[3] Asymmetric methoxyselenenylations with camphor-based selenium electrophiles [J].

Back, TG ;

Nan, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3123-3124

[4] SYNTHESES OF PHENYLKETENE ACETALS VIA ALPHA-BROMOPHENYLACETALDEHYDE ACETALS [J].

BALDWIN, JE ;

WALKER, LE .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (12) :3985-&

[5] Mechanisms of nucleophilic substitutions of acetals [J].

Bull, SD ;

Correia, LMARB ;

Davies, SG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (15) :2231-2233

[6] ENZYME CATALYZED ASYMMETRIC HYDROLYSIS OF CHLORAL ACETYL METHYL ACETAL [J].

CHENEVERT, R ;

DESJARDINS, M ;

GAGNON, R .

CHEMISTRY LETTERS, 1990, (01) :33-34

[7] Asymmetric syntheses of benzaldehyde and o-anisaldehyde methyl isopropyl acetals [J].

Davies, SG ;

Correia, LMARB .

CHEMICAL COMMUNICATIONS, 1996, (15) :1803-1804

[8] THE ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE AND DIOXOLANE ACETALS - SOLUTION STRUCTURE OF THEIR LEWIS ACID COMPLEXES [J].

DENMARK, SE ;

WILLSON, TM ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (26) :9258-9260

[9] STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8089-8110

[10] ON THE STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS - NUCLEOPHILE DEPENDENCE [J].

DENMARK, SE ;

ALMSTEAD, NG .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6485-6487

← 1 2 3 4 →