stereoselective synthesis of saturated heterocycles via palladium catalyzed alkene carboetherification and carboamination reaction通过钯催化的烯烃羰基化和碳化反应立体选择性合成饱和杂环.pdfVIP

ACCOUNT 2913 Stereoselective Synthesis of Saturated Heterocycles via Palladium-Catalyzed Alkene Carboetherification and Carboamination Reactions Palladium-Catalyzed Stereoselective Synthesis of Saturated HeterocyclesJohn P. Wolfe* Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, MI 48109-1055, USA Fax +1(734)6153790; E-mail: jpwolfe@umich.edu Received 9 June 2008 Because of the significance of heterocycles such as those Abstract: The development of palladium-catalyzed carboetherifi- described above, many methods have been developed for cation and carboamination reactions between aryl or alkenyl halides 2–4 and alkenes bearing pendant heteroatoms is described. These trans- their construction. Ring formation is most commonly formations effect the stereoselective construction of useful hetero- achieved through intramolecular SN2 reactions, halocy- cycles, such as tetrahydrofurans, pyrrolidines, imidazolidin-2-ones, clizations, reductive aminations, cycloadditions, or ring- isoxazolidines, and piperazines. The scope, limitations, and applica- closing alkene metathesis reactions. Despite the utility of tions of these reactions are presented, and current stereochemical these strategies, the control of the relative stereochemistry models are described. The mechanism of the product formation, can be problematic in reactions that generate new stereo- which involves an unusual intramolecular syn-insertion of an alkene into a palladium–heteroatom bond, is also discussed in