Synfacts 2009(7): 0750-0750  
DOI: 10.1055/s-0029-1217281
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Allylation of Imines by a Formal Metallo-[3,3]-Rearrangement

Contributor(s): Mark Lautens, Praew Thansandote
M. Takahashi, M. McLaughlin, G. C. Micalizio*
The Scripps Research Institute, Jupiter and Yale University, New Haven, USA
Further Information

Publication History

Publication Date:
22 June 2009 (online)

Significance

A mechanistically unique concept of allylating aryl imines with unactivated allylic alcohols is described using stoichiometric amounts of titanium and magnesium. The reaction scope is broad, allowing for the synthesis of a variety of homoallylic amines in good yields and high anti-selectivity. Of particular note is the reaction’s compatibility with vinyl halides.