Issue 12, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

On the diastereoselectivity of alkylations of bicyclic lactams

Jonathan H. Bailey,a   Andrew T. J. Byfield,a   Philip J. Davis,a   Alison C. Foster,a   Michael Leech,b   Mark G. Moloney,*a   Matthias Müllerb  and  C. Keith Proutb  

* Corresponding authors

a The Department of Chemistry, University of Oxford, Dyson Perrins Laboratory, South Parks Road, Oxford, UK
E-mail: mark.moloney@chem.ox.ac.uk

b Chemical Crystallography Laboratory, University of Oxford, 9 Parks Rd, Oxford, UK

Abstract

The diastereoselectivity in the alkylation of the enolates of bicyclic lactams 2 derived from pyroglutaminol 1a has been found to depend upon the nature of the hemiaminal ether protecting group. Although exo-alkylation has been widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is postulated that this is a result of the opening of the bicyclic structure of the enolate derived from 2d, and the consequent stereoelectronic facilitation of endo-facial attack.

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Article information

DOI
https://doi.org/10.1039/B000432O
Article type
Paper
Submitted
17 Jan 2000
Accepted
19 Apr 2000
First published
30 May 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1977-1982

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On the diastereoselectivity of alkylations of bicyclic lactams

J. H. Bailey, A. T. J. Byfield, P. J. Davis, A. C. Foster, M. Leech, M. G. Moloney, M. Müller and C. K. Prout, J. Chem. Soc., Perkin Trans. 1, 2000, 1977 DOI: 10.1039/B000432O

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