Issue 3, 2016
From the journal:

Organic Chemistry Frontiers

Organocatalytic enantioselective Mukaiyama–Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines†

Jin-Sheng Yua  and  Jian Zhou*ab  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062, China
E-mail: jzhou@chem.ecnu.edu.cn

b State Key Laboratory of Elemento-organic Chemistry, Nankai University, Tianjin 300071, P.R. China

Abstract

The first catalytic asymmetric Mukaiyama–Mannich reaction of fluorinated silyl enol ethers and ketimines is developed. Under the catalysis of hydroquinine derived bifunctional urea, cyclic N-sulfonyl ketimines readily react with fluorinated enol silyl ethers to afford benzosultam based Cα-tetrasubstituted α-amino acid derivatives featuring a fluoroalkyl group in high to excellent yields and stereoselectivities.

Graphical abstract: Organocatalytic enantioselective Mukaiyama–Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines

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Article information

DOI
https://doi.org/10.1039/C5QO00407A
Article type
Research Article
Submitted
02 Dec 2015
Accepted
26 Dec 2015
First published
28 Dec 2015

Org. Chem. Front., 2016,3, 298-303

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Organocatalytic enantioselective Mukaiyama–Mannich reaction of fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines

J. Yu and J. Zhou, Org. Chem. Front., 2016, 3, 298 DOI: 10.1039/C5QO00407A

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