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Synfacts 2006(1): 0046-0046  
DOI: 10.1055/s-2005-921743
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Dynamic Kinetic Asymmetric Allylic Alkylations of Allenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
B. M. Trost*, D. R. Fandrick, D. C. Dinh
Stanford University, USA
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Publication History

Publication Date:
16 December 2005 (online)

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Significance

This report describes a highly enantioselective dynamic kinetic asymmetric allylic alkylation of racemic allenes with amines and malonates. Both reactions give moderate to high yields and high enantioselectivities. The choice of base for the amination reaction proved to be very important. Cs2CO3 gave (S)-allenes whereas the use of an excess of amine gave (R)-allenes (with much lower ee’s though).