Control of four stereocenters in an organocatalytic domino double Michael reaction: efficient synthesis of multisubstituted cyclopentanes.
A highly enantioselective and diastereoselective domino organocatalytic double Michael reaction which provides expedited access to multifunctionalized five-membered rings catalyzed by 9-amino-9-deoxyepiquinine (V) has been developed. Simple operational procedures, high yields (81-92%), excellent enantioselectivity (90-97% ee), diastereoselectivities (95:5->99:1 dr), and immense potential of synthetic versatility of the products render this new methodology highly appealing for asymmetric synthesis.
Tan
Bin
B
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
Shi
Zugui
Z
Chua
Pei Juan
PJ
Zhong
Guofu
G
D002384:Catalysis; D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000737:chemistry*; D013237:Stereoisomerism
C517737:9-amino-9-deoxyepiquinine; D003517:Cyclopentanes; D011807:Quinolizines