Issue 14, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gem-dibromocyclopropanes possessing tethered nucleophiles: the influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

Martin Banwell,*a   Alison Edwards,a   Joanne Harvey,a   David Hocklessa  and  Anthony Willisa  

* Corresponding authors

a Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, Australia

Abstract

The epimeric pairs of ring-fused gem-dibromocyclopropanes 17/18 and 27/28, each of which possesses an internal plane of symmetry and has a tethered carbamate moiety with an associated chiral auxiliary, react with silver perchlorate to give, in a diastereoselective manner, the corresponding pairs of azabicyclic compounds, 19/20 and 29/30 respectively.

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Article information

DOI
https://doi.org/10.1039/B002525I
Article type
Communication
Submitted
30 Mar 2000
Accepted
01 Jun 2000
First published
23 Jun 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2175-2178

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π-Allyl cation cyclisations initiated by silver(I)-promoted electrocyclic ring opening of ring-fused gem-dibromocyclopropanes possessing tethered nucleophiles: the influence of chiral auxiliaries on the diastereoselectivity of cyclisations involving meso-substrates

M. Banwell, A. Edwards, J. Harvey, D. Hockless and A. Willis, J. Chem. Soc., Perkin Trans. 1, 2000, 2175 DOI: 10.1039/B002525I

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