Synfacts 2006(3): 0253-0253  
DOI: 10.1055/s-2006-931960
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Diphenylzinc Addition to Various Aldehydes

Contributor(s): Mark Lautens, Y. Eric Fang
Y.-C. Qin, L. Pu*
University of Virginia, Charlottesville, USA
Further Information

Publication History

Publication Date:
21 February 2006 (online)

Significance

Diphenylzinc addition to aldehydes using a catalytic amount of an H8-binol derivative to afford chiral secondary benzylic alcohols in excellent enantioselectivities and good to excellent yield is reported. Both aromatic and aliphatic aldehydes were tolerated to give uniformly high enantio­selectivity. It is important to perform the reaction in THF since other solvents tend to give much lower enantioselectivities. The catalyst can be easily prepared in excellent yield by reacting H8-binol with morpholinomethanol.