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Synfacts 2008(4): 0417-0417  
DOI: 10.1055/s-2008-1042835
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart · New York

Tripeptides: Efficient Catalysts for 1,4-Addition Reactions to Nitroolefins

Contributor(s):Benjamin List, Subhas Chandra Pan
M. Wiesner, J. D. Revell, H. Wennemers*
University of Basel, Switzerland
Tripeptides as Efficient Asymmetric Catalysts for 1,4-Addition Reactions of Aldehydes to Nitroolefins - A Rational Approach
Angew. Chem. Int. Ed.  2008,  47:  1871-1874  
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Publication History

Publication Date:
19 March 2008 (online)

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Key words

1,4-addition reaction - nitroolefins - peptides - enantioselectivity

Significance

The authors designed tripeptide 1 as an efficient organocatalyst for the asymmetric conjugate addition reactions between aldehydes and nitroolefins. The authors have used N-methyl morpholine (NMM) as an additive for this reaction. After screening different solvents, a mixture of CHCl3 and i-PrOH (9:1) has been found to be the best solvent for this reaction. With 1-5 mol% of catalyst 1, good to high diastereoselectivities (dr = 4:1 to >99:1) and excellent enantioselectivities (er = 91:9 to >99:1) were obtained for different aldehydes and nitroolefins.

Comment

Recently, organocatalytic asymmetric conjugate additions between aldehydes and nitro­olefins have been reported by several groups (see reviews below). This method as reported by the present authors is attractive because of its low catalyst loading (down to 1 mol%).

Reviews

S. B. Tsogoeva Eur. J. Org. Chem. 2007, 1701; S. Sulzer-Mossé, A. Alexakis Chem. Commun. 2007, 3123.

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