Efficient addition reaction of bromonitromethane to aldehydes catalyzed by NaI: A new route to 1-bromo-1-nitroalkan-2-ols under very mild conditions

摘要

A catalytic NaI-mediated novel synthesis of 1-bromo-1-nitroalkan-2-ols was carried out by reaction of bromonitromethane with a variety of aldehydes, under very mild conditions. When the reaction was performed with chiral N, N- dibenzyl alaninal, the corresponding enantiopure ( 1 S, 2 S, 3 S)- 3- dibenzylamino- 1- bromo- 1- nitrobutan- 2- ol was obtained with good stereoselectivity. The structure of this enantiopure bromohydrin was established by X- ray analysis.