Asymmetric Allylation/Pauson-Khand Reaction: A Simple Entry to Polycyclic Amines. Application to the Synthesis of Aminosteroid Analogues

被引：34

作者：

Fustero, Santos ^{[1
,2
]}

Lazaro, Ruben ^{[1
]}

Aiguabella, Nuria ^{[3
]}

Riera, Antoni ^{[3
,4
]}

Simon-Fuentes, Antonio ^{[1
]}

Barrio, Pablo ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Burjassot, Spain

[2] Ctr Invest Principe Felipe, Lab Mol Organ, E-46012 Valencia, Spain

[3] Inst Res Biomed IRB Barcelona, Barcelona 08028, Spain

[4] Univ Barcelona, Dept Quim Organ, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 04期

关键词：

MICHAEL REACTION; EFFICIENT SYNTHESIS; REAGENTS; CYCLOPENTENONES; DERIVATIVES; ROUTE;

D O I：

10.1021/ol500142c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric allylation of o-iodoarylsulfinylimines has been achieved in high diastereoselectivities. The thus-obtained o-iodoarylhomoallylic sulfinamides participate in a subsequent Sonogashira coupling followed by a diastereoselective intramolecular Pauson-Khand reaction. In this way, tricyclic amines showing a unique benzo-fused indenyl backbone were obtained. The methodology has been applied to the synthesis of amino steroid analogues.

引用

页码：1224 / 1227

页数：4

共 42 条

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