Enantioselective synthesis of 2-substituted cyclobutanones

被引：36

作者：

Cho, SY ^{[1
]}

Cha, JK ^{[1
]}

机构：

[1] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 09期

关键词：

D O I：

10.1021/ol005820v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An enantioselective synthesis of 2-substituted cyclobutanones has been achieved by sequential application of the titanium-mediated cyclopropanation of alpha-hydroxy esters and the pinacol-type rearrangement of the resulting alpha-hydroxycyclopropylcarbinols.

引用

收藏

页码：1337 / 1339

页数：3

相关论文

共 36 条

[1]

BATTISTE MA, 1987, CHEM CYCLOPROPYL GRO, pCH6

[2] CYCLOBUTANONES AND CYCLOBUTENONES IN NATURE AND IN SYNTHESIS [J].

BELLUS, D ;

ERNST, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (06) :797-827

[3] A SYNTHESIS OF 2-VINYLCYCLOBUTANONES USING 1-METHOXYCYCLOPROPYLLITHIUM REAGENTS [J].

COHEN, T ;

MATZ, JR .

TETRAHEDRON LETTERS, 1981, 22 (26) :2455-2458

[4] CYCLOHEXENOL ANNULATION VIA THE ALKOXY-ACCELERATED REARRANGEMENT OF VINYLCYCLOBUTANES [J].

DANHEISER, RL ;

MARTINEZDAVILA, C ;

SARD, H .

TETRAHEDRON, 1981, 37 (23) :3943-3950

[5]

Ha J.D., 1999, J AM CHEM SOC, V121, P10012, DOI DOI 10.1021/ja9925958

[6] 1,2-ASYMMETRIC REARRANGEMENTS IN CHIRAL SULFINYLCYCLOPROPANE SYSTEMS - ASYMMETRIC-SYNTHESIS OF ALPHA,ALPHA-DISUBSTITUTED CYCLOBUTANONES [J].

HIROI, K ;

NAKAMURA, H ;

ANZAI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (04) :1249-1250

[7] 2-VINYLCYCLOBUTANONES BY CYCLOADDITION OF VINYLKETENES TO SIMPLE OLEFINS [J].

JACKSON, DA ;

REY, M ;

DREIDING, AS .

HELVETICA CHIMICA ACTA, 1983, 66 (07) :2330-2341

[8]

JULIA M, 1961, B SOC CHIM FR, P1849

[9] NEW, EFFICIENT METHOD FOR THE SYNTHESIS OF ALLYLTITANIUM COMPOUNDS FROM ALLYL HALIDES OR ALLYL ALCOHOL DERIVATIVES VIA OXIDATIVE ADDITION - A HIGHLY EFFICIENT AND PRACTICAL SYNTHESIS OF HOMOALLYL ALCOHOLS [J].

KASATKIN, A ;

NAKAGAWA, T ;

OKAMOTO, S ;

SATO, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) :3881-3882

[10] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

← 1 2 3 4 →