β-Oxy-α-Diazo Carbonyl Compounds. IV. Reaction with Triethyl borane. The influence of the Oxy Group in the Regio- and Stereo-controlled Alkylation on the Diazo Carbon

Article abstract of DOI:10.1016/0040-4039(95)00365-J

The reactions of chiral β-oxy-α-diazocarbonyl compounds with triethylborane were studied.The results of the reactions depend on the particular group used to protect the β-hydroxyl function.Thus, hindered protecting groups lead to N-alkylation of the diazo compound.On the other hand, the product with a free hydroxyl group, undergoes C-alkylation in a good yield with full stereoselectivity.