Shipman, Michael, Beadle, Jonathan D., Powell, Nicola Helen, Raubo, Piotr and Clarkson, Guy J. (2015) Synthesis of oxetane- and azetidine-containing spirocycles related to the 2,5-diketopiperazine framework. Synlett, 27 (1). pp. 169-172. doi:10.1055/s-0035-1560593 ISSN 0936-5214.

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Abstract

A simple two-step sequence is used to efficiently make novel spirocyclic analogues of the diketopiperazine nucleus. Conjugate addition of chiral α-amino esters to nitroalkenes, generated from oxetan-3-one or N-Boc-azetidin-3-one, followed by nitro group reduction provides, after spontaneous cyclization, the spirocycles in good overall yields. These rigid scaffolds can be functionalized by selective N-alkylations as well as by carbonyl reduction to the corresponding piperazines.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH):	Heterocyclic compounds, Pharmaceutical chemistry
Journal or Publication Title:	Synlett
Publisher:	Georg Thieme Verlag
ISSN:	0936-5214
Official Date:	24 November 2015
Dates:	Date Event 24 November 2015 Published 3 November 2015 Accepted 13 January 2015 Submitted
Volume:	27
Number:	1
Number of Pages:	4
Page Range:	pp. 169-172
DOI:	10.1055/s-0035-1560593
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	AstraZeneca (Firm), Engineering and Physical Sciences Research Council (EPSRC), University of Warwick, Birmingham Science City, Advantage West Midlands (AWM)

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