Regioselective and Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds by NaBH4

Abstract

α,β-unsaturated aldehydes and ketones are regioselectively reduced to the corresponding allylic alcohols withNaBH4/Ba(OAc)2system in CH3CN. This system is also efficient for the chemoselective reduction of enals in the presence of enones at room temperature.

An Eco-Friendly System for Oximation of Organic Carbonyl Compounds Under Microwave Irradiation

“…Recently, the oximation methods has been reviewed 4 . The lack of information for systematic the oximation of carbonyl compounds in water under microwave irradiation and our ongoing attentions to the development of modified methods in organic synthesis [5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23] encouraged us to investigate this transformation with NH 2 OH·HCl under microwave irradiation in water as a green and good solvent for transferring electromagnetic energy into heat and so driving an oximation reaction effectively. Herein, we describe a fast and efficient method for the oximation of varieties of carbonyl compounds such as aldehydes, ketones to the corresponding oximes with NH 2 OH·HCl/H 2 O/MWI system.…”

NaBH4/C: A Convenient System for Reductive Amination of Aldehydes

“…Because, other approaches such as: the reduction of nitro, cyano, azide, carboxamide compounds or the alkylation of amines are often problemssuch as: harsh reaction conditions, overalkylation, low chemical selectivity and generally poor yields. The reductive aminationreactionhas been carried out by sodium borohydridewith different reducing system [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] .But, in continuing our efforts for the development of new reducing systems [16][17][18][19][20][21][22][23][24][25][26][27][28] ,in this context, we have reported the reductive amination reaction of aldehydes with anilines by NaBH 4 /C system in THF.…”

Synthesis of N-citralbenzenamines by NaBH4/B(OH)3System

“…Reduction of α, β-unsaturated carbonyl compounds can follow two pathways: addition to carbonyl group (1,2-reduction) to give allylicproducts or addition to the conjugated double bond (1,4reduction) to give saturated carbonyl compounds. NaBH 4 (common reducing agent) uses for the 1,2-reduction of conjugated carbonyl compounds under different reducing system [1][2][3][4][5][6][7][8][9] . On the other hands, in the synthetic project we needed some N-citralbenzenamines.Also, recently we reported a convenient system for direct reductive amination of aldehydes by NaBH 4 /B(OH) 3 system 10 .…”