title: Facile domino access to chiral bicyclo[3.2.1]octanes and discovery of a new catalytic activation mode.
abstract: A highly enantio- and diastereoselective organocatalytic domino Michael-Henry process for the preparation of synthetically unique and medicinally important bicyclo[3.2.1]octane derivatives with four stereogenic centers including two quaternary stereocenters has been developed. Theoretical DFT calculations on the transition states have been carried out to reveal origins of the excellent stereoselectivities. A novel dual model was thus proposed.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Yunpeng
authors.initials: Y
authors.lastname: Lu
authors.forename: Xiaofei
authors.initials: X
authors.lastname: Zeng
authors.forename: Pei Juan
authors.initials: PJ
authors.lastname: Chua
authors.forename: Guofu
authors.initials: G
authors.lastname: Zhong
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D008958:Models, Molecular; D015394:Molecular Structure; D009795:Octanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D009795:Octanes