92237-22-4Relevant articles and documents
Unusual Stereochemistry in the Copper-catalyses Ring Opening of a Carbohydrate Oxirane with Vinylmagnesium Bromide
Brockway, Carol,Kocienski, Philip,Pant, Chandra
, p. 875 - 878 (2007/10/02)
The oxirane ring of 4,6-O-benzylidene-1,5:2,3-dianhydro-D-allitol (1) opened regio- and stereo-selectively at C-2 with Me2CuLi and allylmagnesium chloride in the presence of catalytic amounts of CuI.With vinylmagnesium bromide, however, the ring opening of (1) was regioselective but a mixture of stereoisomers (10) and (12) was obtained corresponding to retention and inversion at C-2.A mechanism for the formation of the anomalous retention product (12) is proposed.