Reactions of Iminium Ions with Michael Acceptors through a Morita–Baylis–Hillman‐Type Reaction: Enantiocontrol and Applications in Synthesis

Abstract

All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita–Baylis–Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z604715_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.