Deportonation of nitroalkanes by bicyclic amidine and guanidine bases; evidence for molecular recognition within a catalytic cycle for C–C bond formation

…, MA Convery, AP Davis, GD Hosken…

Index: Boyle, Peter H.; Convery, Maire A.; Davis, Anthony P.; Hosken, Gladys D.; Murray, Brian A. Journal of the Chemical Society, Chemical Communications, 1992 , # 3 p. 239 - 242

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Citation Number: 24

Abstract

Evidence from 1H NMR spectroscopy supported by X-ray crystallography, suggests that the bicyclic amidine and guanidine bases 2 and 3 react with nitroalkanes in non-polar organic solvents to give tightly-bound ion pairs 5; it is argued that homochiral analogues of these complexes may prove valuable as intermediates in enantioselective catalytic C–C bond- forming reactions.