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Synfacts 2006(9): 0908-0908  
DOI: 10.1055/s-2006-949234
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Catalyzed Michael Addition of Nitroalkanes to Nitroalkenes

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
S.-F. Lu, D.-M. Du*, J. Xu, S.-W. Zhang
Peking University, P. R. of China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

This is an important synthesis of asymmetric 1,3-dinitro compounds from simple starting materials. This group has used their novel C 2-symmetric bis(oxazoline) and bis(thiazoline) ligands to effect this transformation. High ee values (>90% ee in most cases) and diastereoselectivities (ranging from 3.4:1 to 11.7:1) were obtained for a variety of substrates. Ligand 1a was predominantly used, but it was found that the use of 1b gave lower yields, but was provided higher enantioselectivities in some cases. The utility of these compounds was demonstrated by the reduction to the diamine via Pd/C/H2 system and this diamine was converted into the chiral cyclic thiourea by treatment with CS2.