Issue 26, 2016
From the journal:

Organic & Biomolecular Chemistry

Organocatalytic asymmetric addition of alcohols to cyclic trifluoromethyl ketimines: highly enantioselective synthesis of chiral N,O-ketals†

Ding Zhou,a   Xueting Yu,a   Jian Zhang,a   Wei Wang*ab  and  Hexin Xie*a  

* Corresponding authors

a State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
E-mail: xiehexin@ecust.edu.cn

b Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, New Mexico 87131-0001, USA
E-mail: wwang@unm.edu

Abstract

A highly enantioselective addition of alcohols to cyclic trifluoromethyl ketimines is developed catalyzed by quinine-thiourea, giving biologically interesting N,O-ketals in up to 99% yield and 96% ee.

Graphical abstract: Organocatalytic asymmetric addition of alcohols to cyclic trifluoromethyl ketimines: highly enantioselective synthesis of chiral N,O-ketals

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Article information

DOI
https://doi.org/10.1039/C6OB00890A
Article type
Communication
Submitted
26 Apr 2016
Accepted
16 May 2016
First published
17 May 2016

Org. Biomol. Chem., 2016,14, 6193-6196

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Organocatalytic asymmetric addition of alcohols to cyclic trifluoromethyl ketimines: highly enantioselective synthesis of chiral N,O-ketals

D. Zhou, X. Yu, J. Zhang, W. Wang and H. Xie, Org. Biomol. Chem., 2016, 14, 6193 DOI: 10.1039/C6OB00890A

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