Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates

Minghua Li; Nan Ji; Ting Lan; Wei He; Rui Liu

doi:10.1039/C4RA01390E

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Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates†

Minghua Li,^a Nan Ji,^a Ting Lan,^a Wei He*^a and Rui Liu*^b

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* Corresponding authors

^a Department of Chemistry, School of Pharmacy, Fourth Military Medical University, Xi'an 710032, Shaanxi, China
E-mail: weihechem@fmmu.edu.cn

^b Tangdu Hospital, Fourth Military Medical University, Xi'an 710032, Shaanxi, China
E-mail: liurui2@fmmu.edu.cn

Abstract

The catalytic enantioselective aza-Henry reaction of N-Boc aldimines 2 and 2-nitropropionic acid ethyl ester 3 in the mixed solvents of toluene–saturated brine (10 : 1) was catalyzed by cinchona quaternary ammonium salts to form a new quaternary carbon center. High yields (up to 90%), and excellent enantioselectivities (up to 99% ee) and diastereoselectivity ratio (up to 22 : 1) were successfully obtained with mild conditions.

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Article information

DOI: https://doi.org/10.1039/C4RA01390E
Article type: Paper
Submitted: 18 Feb 2014
Accepted: 16 Apr 2014
First published: 17 Apr 2014

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RSC Adv., 2014,4, 20346-20350

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Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates

M. Li, N. Ji, T. Lan, W. He and R. Liu, RSC Adv., 2014, 4, 20346 DOI: 10.1039/C4RA01390E

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Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates†

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Construction of chiral quaternary carbon center via catalytic asymmetric aza-Henry reaction with α-substituted nitroacetates

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