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Issue 19, 2011
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A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams

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Abstract

A new flexible approach for the stereoselective synthesis of substituted 1H-pyrrol-2(5H)-ones and 3,6-dihydro-1H-pyridin-2-ones has been developed. The general strategy employed the stereoselective reduction of a series of α,β-unsaturated ketones under chelation control to give the corresponding allylic alcohols. Overman rearrangement to install the key C–N bond followed by conversion to either prop-2-enoyl or but-3-enoyl derivatives and a ring closing metathesis reaction gave the target unsaturated γ- and δ-lactams. The synthetic utility of these compounds as building blocks was demonstrated by the preparation of the N-Boc derivative of (−)-coniine.

Graphical abstract: A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams

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Article information


Submitted
26 May 2011
Accepted
28 Jun 2011
First published
29 Jun 2011

Org. Biomol. Chem., 2011,9, 6761-6770
Article type
Paper

A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams

M. Daly, K. Gill, M. Sime, G. L. Simpson and A. Sutherland, Org. Biomol. Chem., 2011, 9, 6761
DOI: 10.1039/C1OB05833A

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