Asymmetric palladium-catalyzed hydroarylation of styrenes and dienes

TETRAHEDRON

卷:67

Article

Podhajsky, Susanne M.¹  Iwai, Yasumasa²  Cook-Sneathen, Amanda³  Sigman, Matthew S.¹ 

[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

关键词: Alkenes;    Asymmetric catalysis;    Hydroarylation;    Palladium-catalyzed;   

DOI  :  10.1016/j.tet.2011.02.027

来源: Elsevier

【 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.

【 授权许可】

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