Issue 2, 2012
From the journal:

Organic & Biomolecular Chemistry

Asymmetric α-2-tosylethenylation of N,N-dialkyl-l-amino acid estersvia the formation of non-racemic ammonium enolates†

Eiji Tayama,*a   Tomohito Igarashi,a   Hajime Iwamotoa  and  Eietsu Hasegawaa  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Niigata University, Niigata, Japan
E-mail: tayama@chem.sc.niigata-u.ac.jp
Fax: +81 25 262 7741

Abstract

Asymmetric α-2-tosylethenylation of (S)-2-(pyrrolidin-1-yl)propanoic acid esters was shown to produce good yields with high enantioselectivities. The reaction proceeds via the formation of a non-racemic ammonium enolate without an external source of chirality.

Graphical abstract: Asymmetric α-2-tosylethenylation of N,N-dialkyl-l-amino acid estersvia the formation of non-racemic ammonium enolates

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Article information

DOI
https://doi.org/10.1039/C1OB06074K
Article type
Paper
Submitted
04 Jul 2011
Accepted
26 Sep 2011
First published
27 Sep 2011

Org. Biomol. Chem., 2012,10, 339-345

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Asymmetric α-2-tosylethenylation of N,N-dialkyl-L-amino acid estersvia the formation of non-racemic ammonium enolates

E. Tayama, T. Igarashi, H. Iwamoto and E. Hasegawa, Org. Biomol. Chem., 2012, 10, 339 DOI: 10.1039/C1OB06074K

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