Issue 12, 2003
From the journal:

Chemical Communications

Origin of 1, 3-induction in the addition of alkyl lithium to imines bearing an N-stereogenic center

Nancy,a   Soma Ghosh,a   Nishan Singh,a   Gurmeet Kaur Nanda,a   P. Venugopalan,a   Prasad V. Bharatamb  and  Sanjay Trehan*a  

* Corresponding authors

a Department of Chemistry, Panjab University, Chandigarh-160 014, India
E-mail: trehan_s@yahoo.com

b Department of Chemistry, Guru Nanak Dev University, Amritsar-143 005, India

Abstract

The origin of diastereoselectivity in the addition of alkyl lithium to chiral Schiff bases has been investigated experimentally and theoretically and the formation of the major diastereomer can be explained from the energy minimized structure of the Schiff base in which the phenyl group has been found to orient in such a manner that it posed lesser steric hindrance to the incoming nucleophile as compared to the alkyl group

Graphical abstract: Origin of 1, 3-induction in the addition of alkyl lithium to imines bearing an N-stereogenic center

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Article information

DOI
https://doi.org/10.1039/B300478C
Article type
Communication
Submitted
14 Jan 2003
Accepted
11 Apr 2003
First published
16 May 2003

Chem. Commun., 2003, 1420-1421

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Origin of 1, 3-induction in the addition of alkyl lithium to imines bearing an N-stereogenic center

Nancy, S. Ghosh, N. Singh, G. Kaur Nanda, P. Venugopalan, P. V. Bharatam and S. Trehan, Chem. Commun., 2003, 1420 DOI: 10.1039/B300478C

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