Synfacts 2007(8): 0831-0831  
DOI: 10.1055/s-2007-968728
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Mixed Organobismuth/Dialkylzinc Reagents for Aryl Transfers

Contributor(s): Mark Lautens, Praew Thansandote
I. Sato*, Y. Toyota, N. Asakura
Kwansei Gakuin University, Hyogo, Japan
Further Information

Publication History

Publication Date:
24 July 2007 (online)

Significance

The authors have developed a mixed triarylbismuthane/dialkylzinc system for catalytic aryl transfer to aromatic aldehydes. The organobismuth and dialkylzinc reagents are needed in stoichiometric amounts and the catalytic component is a chiral β-amino alcohol. The reaction is under catalyst control, except in the case of benzaldehyde where the R-configuration is obtained with the S-catalyst. The scope encompasses simple substitutions of the aryl ring of the aldehydes with good to excellent yields and enantioselectivities observed.