Diastereoselective cycloadditions involving methyleneaziridines: Reactions with tetracyanoethylene

M Shipman, T M Ross, A M Z Slawin

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

2-Methyleneaziridines 2a-e containing a stereogenic centre on the N-substitutent undergo [2 pi+2 pi] cycloadditions with tetracyanoethylene to produce diastereomeric 5-azaspiro[3.2]hexanes 3a-e and 4a-e in moderate to good yields (32-82%). The diastereoselectivity of these cycloadditions (12-68% de) is shown to be dependent on the nature of the N-substitutent; The structure of 5-azaspiro[3.2]hexane 4a has been unambiguously determined by X-ray crystallography. (C) 1999 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)6091-6092
Number of pages2
JournalTetrahedron Letters
Volume40
Issue number33
Publication statusPublished - 13 Aug 1999

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