title: A One-Pot Tandem Strategy in Catalytic Asymmetric Vinylogous Aldol Reaction of Homoallylic Alcohols.
abstract: Reported is a rationally-designed one-pot sequential strategy that allows homoallylic alcohols to be employed in a catalytic, asymmetric, direct vinylogous aldol reaction with a series of activated acyclic ketones, including trifluoromethyl ketones, γ-ketoesters, and α-keto phosphonates, in high yields (up to 95%) with excellent regio- and enantio-selectivity (up to 99% ee). This modular combination, including Jones oxidation and asymmetric organocatalysis, has satisfactory compatibility and reliability even at a 20 mmol scale, albeit without intermediary purification.
authors.affiliation: School of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, China. hxfst@eyou.com.
authors.forename: Xufeng
authors.initials: X
authors.lastname: Hou
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, China. jzzhenu@163.com.
authors.forename: Zhenzhong
authors.initials: Z
authors.lastname: Jing
authors.affiliation: Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, China. bxb1990@163.com.
authors.forename: Xiangbin
authors.initials: X
authors.lastname: Bai
authors.affiliation: School of Chemistry and Chemical Engineering, Xuchang University, Xuchang 461000, China. chmjzy@163.com.|Key Laboratory of Natural Medicine and Immuno-Engineering of Henan Province, Henan University, Jinming Campus, Kaifeng 475004, Henan, China. chmjzy@163.com.
authors.forename: Zhiyong
authors.initials: Z
authors.lastname: Jiang
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis*; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D007659:Ketones / Q000737:chemistry
chemical_list: D000438:Alcohols; D000447:Aldehydes; D007659:Ketones; C116609:3-hydroxybutanal
keywords: asymmetric organocatalysis; cascade; homoallylic alcohols; oxidation; vinylogous aldol reactions