Rhodium-catalyzed intramolecular hydroacylation of 5-and 6-alkynals:: Convenient synthesis of α-alkylidenecycloalkanones and cycloalkenones

被引：65

作者：

Takeishi, K ^{[1
]}

Sugishima, K ^{[1
]}

Sasaki, K ^{[1
]}

Tanaka, K ^{[1
]}

机构：

[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, Koganei, Tokyo 1848588, Japan

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2004年 / 10卷 / 22期

关键词：

aldehydes; alkynes; cyclization; hydroacylation; rhodium;

D O I：

10.1002/chem.200400679

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel intramolecular hydroacylation of 5- and 6-alkynals leading to alpha-alkylidenecycloalkanones was accomplished by using cationic a rhodium(I)/BINAP complex. For all cyclizations described, a single (E)-olefin isomer was obtained. At elevated temperature, hydroacylation and double bond migration of 5- and 6-alkynals proceeded in a one-pot reaction to give cycloalkenones. An intramolecular hydroacylation of a 7-alkynal was unsuccessful. This method represents an attractive new route to highly functionalized alpha-alkylidenecycloalkanones and cycloalkenones.

引用

页码：5681 / 5688

页数：8

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