Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes

被引：81

作者：

Podhajsky, Susanne M. ^{[1
]}

Iwai, Yasumasa ^{[2
]}

Cook-Sneathen, Amanda ^{[3
]}

Sigman, Matthew S. ^{[1
]}

机构：

[1] Univ Utah, Dept Chem, Salt Lake City, UT 84112 USA

[2] Kyorin Pharmaceut Co Ltd, Nogi, Tochigi 3290114, Japan

[3] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

TETRAHEDRON | 2011年 / 67卷 / 24期

关键词：

Alkenes; Asymmetric catalysis; Hydroarylation; Palladium-catalyzed; OXIDATIVE KINETIC RESOLUTION; WACKER-TYPE CYCLIZATION; SECONDARY ALCOHOLS; TERMINAL OLEFINS; MOLECULAR-OXYGEN; BORONIC ESTERS; HECK REACTION; ALKENES; LIGAND; (-)-SPARTEINE;

D O I：

10.1016/j.tet.2011.02.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkenes are desirable and highly versatile starting materials for organic transformations, and well-known substrates for palladium catalysis. Typically, these reactions result in the formation of a new alkene product via beta-hydride elimination. In contrast to this scenario, our laboratory has been involved in the development of alkene hydro- and difunctionalization reactions, where beta-hydride elimination can be controlled. We report herein the development of an asymmetric palladium-catalyzed hydroarylation, which yields diarylmethine products in up to 75% ee. Interestingly, a linear free energy relationship is observed between the steric bulk of the ligand within a certain range and the ee of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4435 / 4441

页数：7

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