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
收藏
页码：3762 / 3765
页数：4
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