Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins

被引：39

作者：

Cao, Ziping ^{[1
]}

Zhu, Hongbo ^{[1
]}

Meng, Xin ^{[1
]}

Tian, Laijin ^{[1
]}

Sun, Xuejun ^{[1
]}

Chen, Guang ^{[1
]}

You, Jinmao ^{[1
]}

机构：

[1] Qufu Normal Univ, Sch Chem & Chem Engn, Key Lab Pharmaceut Intermediates & Anal Nat Med, Key Lab Life Organ Anal, Qufu 273165, Shandong, Peoples R China

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 27期

关键词：

alkynylbenzylaldehyde; bridgehead; diene; gold; polycycles; INTRAMOLECULAR WITTIG REACTION; POLYCYCLIC RING-SYSTEMS; ANTI-BREDT COMPOUND; O-ALKYNYLBENZALDEHYDES; 4+2 BENZANNULATION; DOUBLE-BONDS; CYCLIZATION; CYCLOADDITION; ALKENES; DERIVATIVES;

D O I：

10.1002/chem.201601430

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An unprecedented access to strained tetracyclic bridgehead alkenes by reaction of easily accessible ortho-alkynylarylaldehydes with conjugated dienes is described. The process involves a chemo-and stereo-selective, gold-catalyzed, tandem intermolecular [3+2] cycloaddition/Prins-type ring-closing reaction that allows generating structural complexity in a straightforward manner. This approach for the preparation of anti-Bredt compounds is synthetically superior to those previously reported: the procedure is easy to implement, operates under mild experimental conditions, is efficient, and exhibits a good substrate scope.

引用

页码：9125 / 9129

页数：5

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