Chapter

Synthesis of Heterocycles via Metal-Catalyzed Reactions that Generate One or More Carbon-Heteroatom Bonds

Volume 32 of the series Topics in Heterocyclic Chemistry pp 77-107

Date:

Synthesis of Heterocycles via Palladium-Catalyzed Wacker-Type Oxidative Cyclization Reactions of Hydroxy- and Amino-Alkenes

  • Nicholas A. ButtAffiliated withDepartment of Chemistry and Chemical Engineering, Shanghai Jiao Tong University
  • , Wanbin ZhangAffiliated withDepartment of Chemistry and Chemical Engineering, Shanghai Jiao Tong University Email author 

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Abstract

Oxygen and nitrogen containing heterocyclic compounds are some of the most important and prominent structures found in biologically active natural and synthetic products, thus their synthesis is of paramount importance to the chemical community. One particularly important route to the synthesis of these structures is that of Wacker-type oxidative cyclizations. Palladium-catalyzed oxidative cyclizations represent an efficient and simple procedure for the synthesis of a variety of heterocyclic structures. The catalytic system can be fine-tuned to promote different oxidative transformations and to induce asymmetry in to the cyclized products, either via the use of chiral ligands or by manipulating chirality present in the starting substrate.

Graphical Abstract

https://static-content.springer.com/image/chp%3A10.1007%2F7081_2013_102/MediaObjects/306349_1_En_102_Figa_HTML.gif

Keywords

Cyclization Heterocycles Oxidation Palladium Wacker