Enantioselective Oxidative Homocoupling and Cross-Coupling of 2-Naphthols Catalyzed by Chiral Iron Phosphate Complexes

被引：199

作者：

Narute, Sachin ^{[1
]}

Parnes, Regev ^{[1
]}

Toste, F. Dean ^{[2
]}

Pappo, Doron ^{[1
]}

机构：

[1] Ben Gurion Univ Negev, Dept Chem, IL-84105 Beer Sheva, Israel

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 50期

关键词：

TRANSITION-METAL CATALYSIS; DUAL ACTIVATION MECHANISM; PHASE-TRANSFER CATALYST; ASYMMETRIC CATALYSIS; BRONSTED ACID; PHOSPHORIC-ACIDS; VANADIUM CATALYSTS; BINOL DERIVATIVES; REDOX PROPERTIES; FLUORINATION;

D O I：

10.1021/jacs.6b11198

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Novel chiral iron phosphate complexes were prepared as catalysts for asymmetric oxidative coupling reactions. These catalysts were applied for the synthesis of enantio-enriched C-1- and C-2-symmetric BINOLs, in which the 3 and 3' positions are available for chemical modifications. It was proposed that the reaction takes place via an oxidative radical-anion coupling mechanism. A destructive BINOL racemization that competes with the enantioselective oxidative coupling of 2-naphthols was revealed, thereby offering new insights into this highly important reaction.

引用

页码：16553 / 16560

页数：8

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