Issue 68, 2013
From the journal:

Chemical Communications

Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl aminesvia asymmetric addition of silyl dienolates to fluorinated sulfinylimines†

Yingle Liu,a   Jiawang Liu,a   Yangen Huanga  and  Feng-Ling Qing*ab  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, 2999 North Renmin Road, Shanghai 201620, China

b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 Lingling Road, Shanghai 200032, China
E-mail: flq@mail.sioc.ac.cn

Abstract

A tunable and highly regio- and diastereoselective addition of acyclic silyl dienolates 2 to several α-fluoroalkyl sulfinylimines 1 was developed. By appropriate choice of the Lewis acid catalyst, two new chiral α-fluoroalkyl amines 3 and 4 were obtained in good yields and excellent diastereoselectivities (up to >99 : 1 dr), respectively.

Graphical abstract: Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines

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Article information

DOI
https://doi.org/10.1039/C3CC43741H
Article type
Communication
Submitted
18 May 2013
Accepted
20 Jun 2013
First published
21 Jun 2013

Chem. Commun., 2013,49, 7492-7494

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Lewis acid-catalyzed regioselective synthesis of chiral α-fluoroalkyl amines via asymmetric addition of silyl dienolates to fluorinated sulfinylimines

Y. Liu, J. Liu, Y. Huang and F. Qing, Chem. Commun., 2013, 49, 7492 DOI: 10.1039/C3CC43741H

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