Issue 7, 2009
From the journal:

Chemical Communications

The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters†

Mi-hyun Kim,a   Sea-hoon Choi,a   Yeon-Ju Lee,a   Jihye Lee,a   Keepyung Nahm,b   Byeong-Seon Jeong,c   Hyeung-geun Park*a  and  Sang-sup Jew*a  

* Corresponding authors

a Research Institute of Pharmaceutical Sciences and College of Pharmacy, Seoul National University, Korea
E-mail: hgpk@snu.ac.kr
Fax: +82 2-872-9129
Tel: +82 2-880-7871

b Department of Chemistry, Yeungnam University, Korea

c College of Pharmacy, Yeungnam University, Korea

Abstract

The phase-transfer catalytic alkylation of N,N-dialkylmalonamic tert-butyl esters in the presence of 1 mol% of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded highly enantioselective (S)-mono-α-alkylated products (up to 96% ee), which could be readily converted into versatile chiral building blocks without loss of chirality.

Graphical abstract: The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters

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Article information

DOI
https://doi.org/10.1039/B821468A
Article type
Communication
Submitted
01 Dec 2008
Accepted
17 Dec 2008
First published
14 Jan 2009

Chem. Commun., 2009, 782-784

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The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters

M. Kim, S. Choi, Y. Lee, J. Lee, K. Nahm, B. Jeong, H. Park and S. Jew, Chem. Commun., 2009, 782 DOI: 10.1039/B821468A

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