G. Pandey, A. Gaikwad, S. Gadre
Sep 1, 2012
Citations
0
Influential Citations
3
Citations
Journal
Asian Journal of Organic Chemistry
Abstract
Designed scaffold dimethyl [(2R,3R,5S)-5-phenylmorpholine-2,3-diyl]diacetate was synthesized in optically pure form by photoinduced one-electron reductive β-activation of an α,β-unsaturated carbonyl moiety for stereoselective CC bond formation. Use of the morpholine derivative as a “chemical multitalent” is demonstrated by its easy transformation to valuable heterocyclic building blocks such as methyl [(2R,3S)-3-hydroxy-5-oxopyrrolidin-2-yl]acetate, methyl [(2R,3S)-3-amino-5-oxotetrahydrofuran-2-yl]acetate, (3R,4S)-4-aminohexane-1,3,6-triol, and 2-[(2R,3S)-3-aminotetrahydrofuran-2-yl]ethanol.