The first general method for Z-selective olefination of acylsilanes via ynolate anions providing multisubstituted alkenes

被引：77

作者：

Shindo, M

Matsumoto, K

Mori, S

Shishido, K

机构：

[1] Univ Tokushima, Inst Mat Resources, Tokushima 7708505, Japan

[2] Ibaraki Univ, Dept Environm Sci, Mito, Ibaraki 3108512, Japan

[3] Japan Sci & Technol Corp, PRESTO, Mito, Ibaraki 3108512, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 24期

关键词：

D O I：

10.1021/ja026275r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We have developed the first general method for a stereoselective olefination of acylsilanes via ynolate anions to produce (Z)-ß-silyl-α,β-unsaturated ester, which leads to tri- and tetrasubstituted alkenes. Copyright © 2002 American Chemical Society.

引用

收藏

页码：6840 / 6841

页数：2

相关论文

共 42 条

[1] Reaction of ynolate anions derived from silylketenes with electrophiles: A facile preparation of silyl ynol ethers and functionalized silylketenes [J].

Akai, S ;

Kitagaki, S ;

Naka, T ;

Yamamoto, K ;

Tsuzuki, Y ;

Matsumoto, K ;

Kita, Y .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (14) :1705-1709

[2] VINYLSILANE-TERMINATED AND ALKYNYLSILANE-TERMINATED CYCLIZATION REACTIONS [J].

BLUMENKOPF, TA ;

OVERMAN, LE .

CHEMICAL REVIEWS, 1986, 86 (05) :857-873

[3]

Brook M. A, 2000, SILICON ORGANIC ORGA

[4] Electronic control of stereoselectivities of electrocyclic reactions of cyclobutenes: A triumph of theory in the prediction of organic reactions [J].

Dolbier, WR ;

Koroniak, H ;

Houk, KN ;

Sheu, CM .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (10) :471-477

[5] ORGANIC MATERIALS FOR REVERSIBLE OPTICAL-DATA STORAGE [J].

FERINGA, BL ;

JAGER, WF ;

DELANGE, B .

TETRAHEDRON, 1993, 49 (37) :8267-8310

[6] Stereochemical control in organic synthesis using silicon-containing compounds [J].

Fleming, I ;

Barbero, A ;

Walter, D .

CHEMICAL REVIEWS, 1997, 97 (06) :2063-2192

[7] SELECTIVE FORMATION OF ALKENES FROM TRIMETHYLSILYLMETHYL KETONES AND FROM ACYLSILANES [J].

FURSTNER, A ;

KOLLEGGER, G ;

WEIDMANN, H .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1991, 414 (03) :295-305

[8] Total syntheses of justicidin B and retrojusticidin B using a tandem Horner-Emmons-Claisen condensation sequence [J].

Harrowven, DC ;

Bradley, M ;

Castro, JL ;

Flanagan, SR .

TETRAHEDRON LETTERS, 2001, 42 (39) :6973-6975

[9]

HATANAKA Y, 1991, SYNLETT, P845

[10]

HOPPE I, 1979, LIEBIGS ANN CHEM, P219

← 1 2 3 4 5 →