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Synthesis and rhodium complexation of enantiomerically enriched bicyclo[3.3.1]nona-2,6-diene

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
19
Issue
11
Identifiers
DOI: 10.1016/j.tetasy.2008.05.009
Disciplines
  • Chemistry

Abstract

Abstract Enantiomerically enriched ( S, S)-bicyclo[3.3.1]nona-2,6-diene has been synthesised from the readily available diketone ( S, S)-bicyclo[3.3.1]nonane-2,6-dione. The stereochemical purity is maintained on complexation to rhodium. There is a very strong preference for the formation of the homochiral over the heterochiral (alkene) 2Rh + OTf − complex; the self-recognition involved can be rationalised by analysis of DFT calculations.

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