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Synfacts 2008(5): 0530-0530  
DOI: 10.1055/s-2008-1072676
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Morita-Baylis-Hillman Reaction of Aryl Aldehydes

Contributor(s): Benjamin List, Steffen Müller
M. Shi*, X.-G. Liu
Shanghai Institute of Organic Chemistry and East China University of Science and Technology, Shanghai, P. R. of China
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Publication History

Publication Date:
23 April 2008 (online)

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Significance

New axially chiral bis(thio)urea cata­lysts have been prepared by the reaction of iso(thio)cyanates with H8-BINAM derivatives. These and some already known derivatives were applied to asymmetric MBH reactions of different aryl aldehydes and 2-cyclohexen-1-one. The corresponding β-keto allylic alcohols were obtained in moderate to excellent yields and enantiomeric ratios of up to 94:6. The best results were achieved using catalyst 1 (20 mol%) and DABCO (20 mol%) as cocatalyst in toluene at ambient temperature. Using 2-cyclopentene-1-one as nucleophile instead decreased the yields and enantiomeric ratios significantly.