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Transition‐Metal‐Free Coupling Reaction of Vinylcyclopropanes with Aldehydes Catalyzed by Tin Hydride
Author(s) -
Ieki Ryosuke,
Kani Yuria,
Tsunoi Shinji,
Shibata Ikuya
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406496
Subject(s) - electrophile , catalysis , hydride , tin , chemistry , transition metal , allylic rearrangement , cycloaddition , combinatorial chemistry , coupling reaction , metal , organic chemistry
Abstract Donor–acceptor cyclopropanes are useful building blocks for catalytic cycloaddition reactions with a range of electrophiles to give various cyclic products. In contrast, relatively few methods are available for the synthesis of homoallylic alcohols through coupling of vinylcyclopropanes (VCPs) with aldehydes, even with transition‐metal catalysts. Here, we report that the hydrostannation of vinylcyclopropanes (VCPs) was effectively promoted by dibutyliodotin hydride (Bu 2 SnIH). The resultant allylic tin compounds reacted easily with aldehydes. Furthermore, the use of Bu 2 SnIH was effectively catalytic in the presence of hydrosilane as a hydride source, which established a coupling reaction of VCPs with aldehydes for the synthesis of homoallylic alcohols without the use of transition‐metal catalysts. In contrast to conventional catalytic reactions of VCPs, the presented method allowed the use of several VCPs in addition to conventional donor–acceptor cyclopropanes.