Title of article :
Diastereoselective Baylis-Hillman Reaction: First Use of Sugar-Derived (alpha),(beta)-Unsaturated (gamma)-Lactone as Chiral Michael Acceptor
Author/Authors :
Sastry، G. Narahari نويسنده , , Krishna، Palakodety Radha نويسنده , , Reddy، P. Srinivas نويسنده , , Narsingam، M. نويسنده , , Sateesh، B. نويسنده ,
Abstract :
Diastereoselective Baylis-Hillman reaction of sugar-derived (alpha),(beta)-unsaturated (gamma)-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.
Keywords :
sugar-derived (alpha),(beta)-unsaturated (gamma)-lactones , diastereoselective Baylis-Hillman reactions , 2-C-branched glycosides , zwitterion intermediates , Computational studies , transition state structures
Journal title :
Astroparticle Physics
