Nickel-Catalyzed Borylative Ring Opening of Vinyl Epoxides and Aziridines

被引：45

作者：

Crotti, Stefano ^{[1
]}

Bertolini, Ferruccio ^{[1
]}

Macchia, Franco ^{[1
]}

Pineschi, Mauro ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Sci Farmaceut Sede Chim Bioorgan & B, I-56126 Pisa, Italy

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 16期

关键词：

EFFICIENT ROUTE; ALLYL ALCOHOLS; ASYMMETRIC-SYNTHESIS; BIS(PINACOLATO)DIBORON; SUBSTITUTION; TRANSFORMATIONS; REDUCTION; BORATION; DIBORON; ACIDS;

D O I：

10.1021/ol901429g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild ring opening of vinyl epoxides and aziridines with B(2)Pin(2) catalyzed by Ni(O)-Binap affords new functionalized allylic boron derivatives which undergo sequential transformations. The uncatalyzed allylation of aldehydes allows obtaining challenging bishomoallylic alicyclic 1,3-diols and 1,3-amino alcohols with remarkably high stereoselectivities. Valuable trans-bisallylic 1,4-amino alcohols can be obtained by a simple oxidation.

引用

页码：3762 / 3765

页数：4

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