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Synfacts 2006(12): 1245-1245
DOI: 10.1055/s-2006-955639
DOI: 10.1055/s-2006-955639
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York
Diastereoselective Synthesis of Pyrrolidines and Prolines
A. K. Ghosh*, S. Kulkarni, C.-X. Xu, P. E. Fanwick
Purdue University, West Lafayette, USA
Further Information
Publication History
Publication Date:
22 November 2006 (online)
Significance
The report constitutes one of the few multicomponent reactions (MCR) that generate multiple stereocenters. The method created three contiguous stereocenters in a single operation. The rearrangement of furan adduct 5 to pyrrolidine 4 is an extension of a method developed previously by the same group (A. K. Ghosh, C.-X. Xu, S. S. Kulkarni, D. Wink Org. Lett. 2005, 7, 7-10). The reaction can be halted at the THF adduct 5 in the presence of MeCN as an additive. In all cases, the MCR yielded highly substituted proline derivatives 4 and 7 with excellent diastereoselectivity.