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Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds. Issue 21 (26th May 2016)
Record Type:
Journal Article
Title:
Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds. Issue 21 (26th May 2016)
Main Title:
Asymmetric Michael reaction of arylacetyl phosphonates to nitroalkenes with bifunctional amine-thiourea catalyst bearing multiple-hydrogen-bond donor: efficient construction of chiral α-substituted carboxylic ester compounds
Abstract: Catalytic asymmetric Michael addition of arylacetyl phosphonates to nitroalkenes was achieved with a chiral bifunctional amine-thiourea bearing a multiple-hydrogen-bond donor as a catalyst. A range of α-substituted carboxylic ester compounds with contiguous tertiary stereocenters could be smoothly obtained in good yields (up to 85%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 95% ee). The large scale experiment and facile synthesis of a chiral γ-butyrolactam have also been demonstrated. Graphical abstract: