The reported ability of chiral phosphonamide 1 to effect the enantioselective opening of meso epoxides with silicon tetrachloride has not withstood experimental verification by Denmark's group. Having reexamined the ring-opening of cyclooctene oxide, Denmark and co-workers found a serious discrepancy between their results (81-83 % recovery of the epoxide and an essentially racemic product) and those reported by Buono et al. (77 % yield and >99 % ee).
Keywords: Lewis bases; asymmetric catalysis; correspondence; epoxides; ring opening.
© 2001 WILEY-VCH Verlag GmbH, Weinheim, Fed. Rep. of Germany.