螺硼酸酯不对称催化制备（R）-3-氯-苯丙醇

Enantioselective Synthesis of (R)-3-chloro-1-phenyl-1-propanol Catalyzed by Chiral Spiroborate Ester

摘要:

以3-氯-苯丙酮为原料，螺硼酸酯为催化剂，采用不对称催化还原法合成手性中间体（R）-3-氯-苯丙醇。考察了溶剂对催化剂活性的影响以及催化剂用量、硼烷用量和温度对产品纯度和光学纯度的影响。以乙酸乙酯溶剂中制得的手性螺硼酸酯为催化剂，在n（3-氯-苯丙酮）：n（螺硼酸酯）：n（硼烷）=1：0.1：0.6，反应温度5~10℃条件下，产品纯度达99.5%，产品光学纯度96.3% e.e.。

Abstract:

(R)-3-chloro-1-phenyl-1-propanol was enantioselectively synthesized with 3-chloropropiophenone as raw material and spiroborate ester as catalyst. The influence of solvent on catalyst activity and the effects of catalyst dosage, borane dosage and reaction temperature on the purity and optical purity of (R)-3-chloro-1-phenyl-1-propanol were investigated, respectively. With chiral spiroborate ester prepared in ethyl acetate solvent as catalyst, when n(3-chloropropiophenone):n(spiroborate ester):n(borane)=1:0.1:0.6, and temperature 5~10℃, the product purity and optical purity of (R)-3-chloro-1-phenyl-1-propanol reached 99.5% and 96.3% e.e., respectively.