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Synfacts 2011(7): 0788-0788  
DOI: 10.1055/s-0030-1260631
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Dienic Sulfones as Efficient 1,6-Acceptors in the Addition of Aldehydes

Contributor(s): Benjamin List, Steffen Müller
J. J. Murphy, A. Quintard, P. McArdle, A. Alexakis*, J. C. Stephens*
Université de Genève, Switzerland; National University of Ireland Maynooth and National University of Ireland Galway, Ireland
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Publication History

Publication Date:
17 June 2011 (online)

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Significance

The authors report the reaction ­between 1,3-bis(sulfonyl)butadienes 1 and aldehydes 2 to give cyclohexadienes in high yields and consistently high diastereo- and enantioselectivities. Prolinol silyl ether 3 (30 mol%) was identified to be a suitable catalyst for this transformation. The suggested mechanism involves a unprecedented 1,6-addition of the enamine derived from 2 and 3 to diene 1, followed by an intramolecular Mannich-type reaction and subsequent elimination of the catalyst. Notably no 1,4-addition product was ever observed in these reactions.