Regioselective 1,2-reduction of conjugated enones and enals with sodium monoacetoxyborohydride: preparation of allylic alcohols

Regioselective and Chemoselective Reduction of α,β-Unsaturated Carbonyl Compounds by NaBH4Mohamadi1, Setamdideh2, Khezri3 2013Organic Chemistry International9060View full textAdd to dashboardCite

“…To highlight the efficiency of our system, we compared our results with other reported reducing systems in the literature such as Ph 3 PMeBH 4 [21,22], NaBH 3 (OAc) [3], NaBH 3 CN [23], Li--BuBH 3 [6], (i-PrO) 2 TiBH 4 [24], NaBH 4 /C [25], NaBH 4 /wet SiO 2 [26], NaBH 4 /Dowex1-8x [27], and NaBH 4 /DOWEX(R)50WX4 [28] (Table 4). Some of the reducing systems have been used in more hydride anions versus one molar equivalent of carbonyl group.…”

“…Reduction of , -unsaturated carbonyl compounds widely has been carried out by different reducing agents. This reaction is highly solvent dependent and generally does not result in a useful regioselectivity [1][2][3]. It can follow two pathways: addition to carbonyl group (1,2-reduction) to give allylic alcohols or addition to the conjugated double bond (1,4-addition) to give saturated carbonyl compounds.…”

Poly(diallyldimethylammonium chloride) as an Efficient Phase Transfer Catalyst in Solvent‐Free Reduction of Carbonyl Compounds with NaBH4

“…This achievement is synthetically very important, 8 especially, when the reduction of α,β-unsaturated carbonyl compounds with NaBH 4 is highly solvent dependent and generally does not result in a useful regioselectivity. 9 Selective 1,2-reduction is usually achieved using modified hydride reagents, which are formed by the replacement of hydride with sterically bulky substituents or electron-withdrawing groups in order to discriminate between the structural or electronic environments of the carbonyl functionality.…”

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 .…”