Asymmetric supramolecular catalysis: a bio-inspired tool for the high asymmetric induction in the enamine-based Michael reactions.
King size: Utilization of large-size supramolecular rings in the pre-transition state (pre-TS) of enamine-based Michael reactions for high asymmetric induction is described. Enantiomerically pure, druglike hexahydroxanthenes with three contiguous stereocenters were synthesized through supramolecular catalysis by D-proline and quinine-NH-thiourea followed by reductive etherification from simple precursors under mild conditions (see scheme).
Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046, India. ramchary.db@gmail.com
Dhevalapally B
DB
Ramachary
Rajasekar
R
Sakthidevi
Kodambahalli S
KS
Shruthi
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003512:Cyclohexanones / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
D003512:Cyclohexanones; D010636:Phenols; D014966:Xanthenes; D011392:Proline; D013890:Thiourea