A Rh-Catalyzed Cycloisomerization/Diels-Alder Cascade Reaction of 1,5-Bisallenes for the Synthesis of Polycyclic Heterocycles

被引：21

作者：

Artigas, Albert ^{[1
]}

Vila, Jordi ^{[1
]}

Lledo, Agusti ^{[1
]}

Sola, Miguel ^{[1
,2
]}

Pla-Quintana, Anna ^{[1
]}

Roglans, Anna ^{[1
,2
]}

机构：

[1] Univ Girona UdG, IQCC, C Maria Aurelia Co 69, Girona 17003, Catalunya, Spain

[2] Univ Girona UdG, Dept Quim, C Maria Aurelia Co 69, Girona 17003, Catalunya, Spain

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 17期

关键词：

2+2+2 CYCLOADDITION; CYCLIZATION REACTIONS; CHIRAL INDUCTION; ALLENES; DERIVATIVES; SCAFFOLDS; ACCESS;

D O I：

10.1021/acs.orglett.9b02032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel methodology to transform bisallenes into a variety of polycyclic derivatives employing rhodium(I) catalysis has been developed. This transformation encom-passes an intramolecular Rh-catalyzed cycloisomerization of bisallenes 1 to deliver a reactive cycloheptadiene, which concomitantly undergoes a regioselective [4 + 2] cyclo-addition with alkenes. A complete mechanistic study of this transformation has been undertaken including DFT calculations. Overall, the methodology presented here constitutes a new and straightforward entry to polycyclic dihydroazepine and dihydrooxepine derivatives employing catalytic methods.

引用

页码：6608 / 6613

页数：6

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