posted on 1999-10-22, 00:00authored byQian 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 5−7 provided 2,3,5-trisubstituted pyrrolidines that were subjected to reductive desulfonylation to give trans-2,5-disubstituted pyrrolidines 11−13, 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.