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Synfacts 2009(3): 0328-0328  
DOI: 10.1055/s-0028-1087728
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Allylic-Allylic Alkylation

Contributor(s): Benjamin List, Ilija Èorić
H.-L. Cui, J. Peng, X. Feng, W. Du, K. Jiang, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publikationsdatum:
19. Februar 2009 (online)

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Significance

A highly enantioselective allylic-­allylic alkylation of α,α-dicyanoalkenes and ­Morita-Baylis-Hillman carbonates has been described. The combination of tertiary amine catalyst (DHQD)2AQN and (S)-BINOL was necessary for high yields, although the enantioselectivity was not significantly influenced by the addition of the Brønsted acid co-catalyst. In general, a very high diastereoselectivity (>99:1) was observed. Products 3 were converted into several complex chiral frameworks.