☆ 4.7 Article

Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes

JOURNAL OF ORGANIC CHEMISTRY (2013)

期刊

JOURNAL OF ORGANIC CHEMISTRY

卷 78, 期 21, 页码 10763-10775

出版社

AMER CHEMICAL SOC

DOI: 10.1021/jo401758v

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类别

Chemistry, Organic

资金

JSPS
KAKEHNHI [21590003]
Uehara Memorial Foundation
Grants-in-Aid for Scientific Research [25460004] Funding Source: KAKEN

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Reagent

摘要

The carbocyanative cyclization of allene-ynes and bis-allenes under nickel catalysis is described. The key steps are the regioselective hydronickelation of allenes and subsequent cyclization via carbometalation. The former step determines the reaction pathway, and the latter controls the stereochemistry of substituted olefins. The products are useful carbo- and heterocycles that include a cyano group, functionalized double bonds, and quaternary carbons.

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