Nickel-Catalyzed Borylative Ring Opening of Vinyl Epoxides and Aziridines

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• 作者：Stefano Crotti ; Ferruccio Bertolini ; Franco Macchia ; Mauro Pineschi
• 刊名：Organic Letters
• 出版年：2009
• 出版时间：August 20, 2009
• 年：2009
• 卷：11
• 期：16
• 页码：3762-3765
• 全文大小：131K
• 年卷期：v.11,no.16(August 20, 2009)
• ISSN：1523-7052

文摘

A mild ring opening of vinyl epoxides and aziridines with B₂Pin₂ catalyzed by Ni(0)-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.