Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling

A deuterium-labeling reaction of nitro-alkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled beta-nitroalcohols in high yields and high deuterium contents. beta-Deuterated beta-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and alpha-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired beta-deuterated nitroalcohol derivatives with high enantioselectivities.