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Allylsilane–Vinylarene Cross‐Metathesis Enables a Powerful Approach to Enantioselective Imine Allylation
Author(s) -
Huber John D.,
Perl Nicholas R.,
Leighton James L.
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200705621
Subject(s) - imine , enantioselective synthesis , metathesis , computer science , chemistry , salt metathesis reaction , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , polymerization , polymer
“ Cinnamylation‐flavored” synthesis : Cross‐metathesis (CM) reactions between an allylsilane and vinylarenes enable the rapid generation of various cinnamylsilanes, which may be used in situ for the highly enantioselective, and diastereodivergent, cinnamylation of imines (see example in scheme). Under this new, simple, and efficient protocol, the potential of imine cinnamylation to produce stereochemically and functionally complex products has been more fully realized. Ar=thienyl, Ar′=2‐hydroxyphenyl.