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Enantioselective Synthesis of Polycyclic Nitrogen Heterocycles by Rh-Catalyzed Alkene Hydroacylation: Constructing Six-Membered Rings in the Absence of Chelation Assistance
Organic Letters ( IF 4.9 ) Pub Date : 2014-07-14 00:00:00 , DOI: 10.1021/ol501869s
Xiang-Wei Du 1 , Avipsa Ghosh , Levi M Stanley
Affiliation  

Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydropyrido[1,2-a]indol-9(6H)ones and 6,7-dihydroindolizin-8(5H)-ones in moderate to high yields with excellent enantioselectivities.

中文翻译:

Rh 催化烯烃氢酰化对映选择性合成多环氮杂环:在没有螯合辅助的情况下构建六元环

报道了N-烯丙基吲哚-2-甲醛和N-烯丙基吡咯-2-甲醛的催化对映选择性加氢酰化。与形成六元环的许多烯烃加氢酰化相反,这些环化过程是在不存在稳定酰基铑(III)氢化物中间体的辅助官能团的情况下发生的。分子内加氢酰化反应以中等至高产率生成具有优异对映选择性的7,8-二氢吡啶并[1,2- a ]吲哚-9(6 H )-酮和 6,7-二氢吲哚嗪-8(5 H )-酮。
更新日期:2014-07-14
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