Allylsilane–Vinylarene Cross-Metathesis Enables a Powerful Approach to Enantioselective Imine Allylation


  • This work was supported by a grant from the NSF (CHE-04-53853) and a Focused Funding Award from Johnson & Johnson. We thank Merck Research Laboratories and Amgen for unrestricted support. J.D.H. was the recipient of an NDSEG Fellowship from the Department of Defense, and N.R.P. was supported by a fellowship provided by Boehringer-Ingelheim.


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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.