A new diastereo- and enantioselective copper-catalyzed conversion of alkynyl epoxides into α-allenic alcohols.

被引：43

作者：

Bertozzi, F

Crotti, P

Macchia, F

Pineschi, M

Arnold, A

Feringa, BL

机构：

[1] Univ Pisa, Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

[2] Univ Groningen, Dept Organ & Mol Inorgan Chem, NL-9747 AG Groningen, Netherlands

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 26期

关键词：

D O I：

10.1016/S0040-4039(99)00905-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral copper complexes of BINOL- and TADDOL derived phosphorus amidites proved to be highly effective catalysts for the alkylation of alkynyl epoxides with dialkylzinc reagents. The corresponding alpha-allenol reaction products (S(N)2'-pathway) were obtained with good to excellent regio- and diastereoselectivity. The e.e. values obtained for this reaction were in the range of 26-38 %. A number of different Cu(II)-complexes were screened as possible catalysts and the results obtained indicate a complete control of the diastereoselectivity with an easy access to both enantioenriched syn and anti-alpha-allenols. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：4893 / 4896

页数：4

共 18 条

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