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Synfacts 2011(7): 0790-0790  
DOI: 10.1055/s-0030-1260635
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

A Catalytic Asymmetric Darzens Reaction under Phase-Transfer Conditions

Contributor(s): Benjamin List, Steffen Müller
Y. Liu, B. A. Provencher, K. J. Bartelson, L. Deng*
Brandeis University, Waltham, USA and Dalian Institute of Chemical Physics, P. R. of China
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

Deng and co-workers report the catalytic asymmetric Darzens reaction between cyclic and acyclic α-chloro ketones and aliphatic as well as aromatic aldehydes. A systematic tuning of cinchona alkaloid derived quaternary ammonium salts revealed structure 1 as the phase-transfer catalyst of choice. In the presence of lithium hydroxide as stoichiometric base, catalyst 1 provides the desired products in high yields and high enantioselectivities.