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Olefin‐Migrative Cleavage of Cyclopropane Rings through the Nickel‐Catalyzed Hydrocyanation of Allenes and Alkenes
Author(s) -
Hori Hiroto,
Arai Shigeru,
Nishida Atsushi
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201601400
Subject(s) - hydrocyanation , chemistry , cyclopropane , cleavage (geology) , nickel , catalysis , olefin fiber , methylenecyclopropane , bond cleavage , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry) , geotechnical engineering , fracture (geology) , engineering
A nickel‐catalyzed hydrocyanation triggered by hydronickelation of the carbon‐carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio‐ and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl‐ and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes.