Co-reporter: Tao Liu, Youming Wang, Guiping Wu, Haibin Song, Zhenghong Zhou, and Chuchi Tang
pp: 4119-4124
Publication Date(Web):April 5, 2011
DOI: 10.1021/jo2002825
By employing a cinchonine-based thiourea as catalyst, highly enantioselective Michael addition reactions of 2-hydroxy-1,4-naphthoquinone to β,γ-unsaturated α-ketophosphonates were realized. The reaction afforded the corresponding β-substituted carboxylates in excellent yields with high levels of enantioselectivities (94−>99% ee) upon quenching the generated parent structures with DBU and MeOH as a second nucleophile.
