Issue 9, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

Jonathan Clayden,*a   Neil Westlunda  and  Christopher S. Framptonb  

* Corresponding authors

a Department of Chemistry, University of Manchester, Oxford Rd., Manchester, UK

b Roche Discovery Welwyn, 40 Broadwater Rd., Welwyn Garden City, Herts, UK

Abstract

Restricted rotation about the Ar–CO bond means that 1-naphthamides bearing chiral 8-substituents may exist as pairs of diastereoisomeric atropisomers. These atropisomers are formed with good to excellent stereoselectivity for the syn-diastereoisomer by the reaction of 8-formyl-1-naphthamides with organolithiums and Grignard reagents. The reduction of 8-acyl-1-naphthamides also proceeds with syn-selectivity. The product alcohols are prone to lactonisation and also to epimerisation, and some of the apparent diastereoselectivities may be the result of thermodynamic, rather than kinetic, control.

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Article information

DOI
https://doi.org/10.1039/B000670J
Article type
Paper
Submitted
24 Jan 2000
Accepted
10 Mar 2000
First published
18 Apr 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1379-1385

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Atropisomeric diastereoisomers from nucleophilic attack on 8-acyl-1-naphthamides

J. Clayden, N. Westlund and C. S. Frampton, J. Chem. Soc., Perkin Trans. 1, 2000, 1379 DOI: 10.1039/B000670J

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