Copper-Catalyzed Asymmetric 1,4-Hydroboration of Coumarins with Pinacolborane: Asymmetric Synthesis of Dihydrocoumarins

被引：44

作者：

Kim, Hyohyun ^{[1
,2
]}

Yun, Jaesook ^{[1
,2
]}

机构：

[1] Sungkyunkwan Univ, Dept Chem, Suwon 440746, South Korea

[2] Sungkyunkwan Univ, Inst Basic Sci, Suwon 440746, South Korea

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 11-12期

基金：

新加坡国家研究基金会;

关键词：

copper; coumarins; dihydrocoumarins; hydroboration; pinacolborane; reduction; ENDOTHELIN RECEPTOR ANTAGONISTS; ENANTIOSELECTIVE CONJUGATE REDUCTION; ALPHA; BETA-UNSATURATED ESTERS; (R)-TOLTERODINE; HYDROGENATION; 1,4-ADDITION; SULFONES; KETONES; ENONES; ACIDS;

D O I：

10.1002/adsc.201000310

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient asymmetric addition of pinacolborane to 4-substituted coumarins proceeded with high enantioselectivity in the presence of a copper(I)-QuinoxP complex as a catalyst to produce the corresponding 1,4-hydroboration products Treatment of the intermediates with electrophiles, without isolation, resulted in enantioenriched dihydrocoumarins The utility of this protocol was demonstrated in the formal synthesis of biologically active molecules.

引用

页码：1881 / 1885

页数：5

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