Synthesis and rhodium complexation of enantiomerically enriched bicyclo[3.3.1]nona-2,6-diene
Mayr M., Bataille CJR., Gosiewska S., Raskatov JA., Brown JM.
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.