手性化合物1,1′-联二萘酚的合成及其在不对称氧化还原反应中的应用

Synthesis of Chiral Compound 1,1′-Bi-2,2′-Naphthol and Its Application in Asymmetric Oxidation and Reduction Reactions

综述了催化氧化偶联2-萘酚合成外消旋体1,1′-联二萘酚(B INOL)的方法。介绍了制备对映体B INOL的化学拆分法、酶拆分法、不对称催化合成法和酶催化合成法的新进展。介绍了对映体B INOL作为手性试剂在不对称还原前手性羰基化合物为手性醇、不对称还原亚胺为手性氨基化合物、不对称环氧化合成α,β-不饱和化合物以及不对称氧化硫化物反应中的应用。

Synthesis of racemic 1,1＇ - bi - 2,2＇ - naphthol （ BINOL ） by catalytic oxidative coupling of 2 - naphthol was reviewed. Advances in preparation of BINOL enantiomer were introduced, including chemical resolution, enzymatic resolution, asymmetric catalytic synthesis and enzyme - catalyzed synthesis. As chiral reagent, enantiomer BINOL was applied to asymmetrically reduce prechiral carbonyl compound to corresponding chiral alcohol, asymmetrically reduce imine to chiral amide, asymmetric epoxidation to synthesis of α, β - unsaturated compound and asymmetric oxidation of sulfide.