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Synfacts 2005(1): 0145-0145  
DOI: 10.1055/s-2005-872186
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Pd-Catalyzed Asymmetric Allylation of Aldehydes using Allylic Alcohols

Contributor(s): Mark Lautens, Y. Eric Fang
S.-F. Zhu, Y. Yang, L.-X. Wang, B. Liu, Q.-L. Zhou*
Nankai University, P. R. of China
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Publikationsdatum:
21. September 2005 (online)

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Significance

A palladium-catalyzed asymmetric allylation of aldehydes using an umpolung of π-allylpalladium generated from Pd(0), allylic alcohol and Et3B is reported. The chiral spiro monodentate phosphine ligand has proved to be efficient for many aryl, heteroaryl and alkyl aldehydes. Under these conditions, an anti-homoallylic alcohol was obtained in excellent diastereoselectivity and in generally good ee’s.