Bulletin of the Chemical Society of Japan p. 1213 - 1220 (1988)
Update date:2022-08-04
Topics:
Yamashita, Hiroyuki
The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartarates as heterogeneous chiral Lewis acid catalysts.The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartarate, and Zn(II) d-tartarate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42 percent ee, respectively.Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tatratate was studied.
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