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α,β‐Unsaturated δ‐Lactones from Copper‐Catalyzed Asymmetric Vinylogous Mukaiyama Reactions of Aldehydes: Scope and Mechanistic Insights
Author(s) -
BazánTejeda Belén,
Bluet Guillaume,
Broustal Garance,
Campagne JeanMarc
Publication year - 2006
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.200600335
Subject(s) - scope (computer science) , chemistry , aldehyde , catalysis , reactivity (psychology) , copper , silylation , organic chemistry , medicine , alternative medicine , pathology , computer science , programming language
A direct regio‐, diastereo‐, and enantiocontrolled access to α,β‐unsaturated δ‐lactones is described, based on the reaction of a silyl dienolate and an aldehyde in the presence of 10 % of Carreira's catalyst. The scope and limitations of this reaction, as well as mechanistic insights concerning the reactivity of an allyl copper species, are discussed.