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A Versatile Method for the Facile Synthesis of Enantiopure trans- and cis-2,5-Disubstituted Pyrrolidines

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journal contribution
posted on 1999-10-22, 00:00 authored by Qian Wang, N. André Sasaki, Claude Riche, Pierre Potier
Treatment of (2S)-1-O-benzylglycerol-2,3-bistriflate (2) with the trilithiated species of chiral building blocks 57 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 1113, respectively. The same reaction sequence with the (2R)-bistriflate 4 and trilithiated 5 afforded the cis isomer 19. This two-step synthetic mehodology can furnish any one of the four possible diastereomers of enantiopure 2,5-disubstituted pyrrolidines in 60−72% overall yields.

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