Regioselective and Chemoselective Reduction of 𝜶,𝜷-Unsaturated Carbonyl Compounds by NaBH₄/Ba(OAc)₂ as a Reducing System

Table 2

Reduction of α,β-unsaturated carbonyl compounds with NaBH₄/Ba(OAc)₂ as a reducing system in CH₃CN.

Entry	Substrate	Product	Molar ratio^c	Time (min)	Yield (%)^d
1^a	Cinnamaldehyde	3-phenyl-2-propen-1-ol	1 : 0.5 : 0.2	5	94
2^a	Citral	3,7-dimethyl-2,6-octadien-1-ol	1 : 0.5 : 0.2	5	93
3^b	Benzylideneacetone	4-phenyl-3-buten-2-ol	1 : 2 : 0.2	15	95
4^b	Chalcone	1,3-diphenyl-2-propen-1-ol	1 : 2 : 0.2	15	96
5^b	β-ionone	4-(2,6,6-trimethylcyclohex-1-enyl)-3-buten-2-ol	1 : 2 : 0.2	10	97
6^b	2-cyclohexenone	2-cyclohexenol	1 : 2 : 0.2	10	95
7^b	3-methyl-2-cyclopentenone	3-methyl-2-cyclopentenol	1 : 2 : 0.2	10	98

 ^aThe reduction reaction was carried out at room temperature; ^bthe reduction reaction was carried out under reflux conditions. ^cMolar ratio as substrate: NaBH₄ : Ba(OAc)₂; ^dyields refer to isolated pure products.