Facile domino access to chiral bicyclo[3.2.1]octanes and discovery of a new catalytic activation mode.
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.
Tan
Bin
B
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.
Lu
Yunpeng
Y
Zeng
Xiaofei
X
Chua
Pei Juan
PJ
Zhong
Guofu
G
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
D001643:Bridged Bicyclo Compounds; D009795:Octanes