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Synthesis 2005(3): 475-479  
DOI: 10.1055/s-2004-837292
PAPER
© Georg Thieme Verlag Stuttgart · New York

Reductive Cyclisation of Azidolactams with Bu3P/LiAlH4

Gurdeep S. Nandraa, Michael J. Porter*a, Jason M. Elliottb
a Department of Chemistry, University College London, Christopher Ingold Building, 20 Gordon Street, London WC1H 0AJ, UK
Fax: +44(20)76797463; e-Mail: m.j.porter@ucl.ac.uk;
b Merck Sharp & Dohme Research Laboratories, The Neuroscience Research Centre, Terlings Park, Eastwick Road, Harlow, Essex CM20 2QR, UK
Further Information

Publication History

Received 5 October 2004
Publication Date:
16 December 2004 (online)

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Abstract

Octahydropyrrolo[2,3-b]pyrroles were synthesised by treatment of azidolactams successively with tri-n-butylphosphine and LiAlH4.

Key words

azides - lactams - aminals - bicyclic Compounds - heterocycles

    References

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6

Thorsett et al. (ref. [1] ) report a coupling constant of 7 Hz between the ring junction protons in a cis-fused octahydro[2,3-b]pyrrole.

9

The relative stereochemistry of this compound is assigned by analogy to reactions in ref. [7]