Diastereoselective Baylis-Hillman Reaction: First Use of Sugar-Derived α,β-Unsaturated δ-Lactone as Chiral Michael Acceptor

Abstract

Diastereoselective Baylis-Hillman reaction of sugar-derived α,β-unsaturated δ-lactone with several aromatic aldehydes in presence of DABCO (50 mol%) to afford adducts in moderate to good yields (49-75%) with 30-82% de is being reported for the first time. Quantum chemical calculations based on the stabilities of transition structures and on the stabilities of zwitterionic intermediates rationalized the experimental observations.