Organocatalytic Nitroaldol Reaction Associated with Deuterium‐Labeling

Abstract

AbstractA deuterium‐labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium‐labeled β‐nitroalcohols in high yields and high deuterium contents. β‐Deuterated β‐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 α‐keto esters as electrophiles in the presence of a quinine‐derived organocatalyst in deuterium oxide could provide the desired β‐deuterated nitroalcohol derivatives with high enantioselectivities.magnified image