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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. © 2008 Elsevier Ltd. All rights reserved.

Original publication

DOI

10.1016/j.tetasy.2008.05.009

Type

Journal article

Journal

Tetrahedron Asymmetry

Publication Date

16/06/2008

Volume

19

Pages

1328 - 1332