title: Control of four stereocenters in an organocatalytic domino double Michael reaction: efficient synthesis of multisubstituted cyclopentanes.
abstract: 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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, Singapore.
authors.forename: Bin
authors.initials: B
authors.lastname: Tan
authors.forename: Zugui
authors.initials: Z
authors.lastname: Shi
authors.forename: Pei Juan
authors.initials: PJ
authors.lastname: Chua
authors.forename: Guofu
authors.initials: G
authors.lastname: Zhong
mesh_terms: 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
chemical_list: C517737:9-amino-9-deoxyepiquinine; D003517:Cyclopentanes; D011807:Quinolizines