New insights into NIS-promoted aminocyclization. Synthesis of decahydroquinolines from 2-allylcyclohexylamines

被引：18

作者：

Diaba, Faiza ^{[1
]}

Ricou, Eva ^{[1
]}

Bonjoch, Josep ^{[1
]}

机构：

[1] Univ Barcelona, Fac Farm, Lab Quim Organ, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 14期

关键词：

D O I：

10.1021/ol070770g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bishomoallylic secondary amines embodying the 2-allyl-N-benzylcyclohexylamine unit react with NIS to undergo cyclization through 6-endo processes in either the cis or trans series. Nevertheless, when the resulting cis-3-iododecahydroquinolines are treated with Al2O3, the exo derivatives evolve into octahydroindoles and the endo derivatives keep the same backbone, the configuration being retained in the generated alcohols.

引用

页码：2633 / 2636

页数：4

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