American Chemical Society
ol8b00342_si_001.pdf (6.57 MB)

Enantioselective Organocatalyzed Direct α‑Thiocyanation of Cyclic β‑Ketoesters by N‑Thiocyanato­phthalimide

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journal contribution
posted on 2018-02-23, 18:37 authored by Jiashen Qiu, Di Wu, Pran Gopal Karmaker, Hongquan Yin, Fu-Xue Chen
A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.