Rhodium(I)-Catalyzed Intermolecular [2+2+2] Cycloaddition of Allenyl Aldehydes with Alkynes and Related Cyclization

被引：10
|
作者：
Oonishi, Yoshihiro [1 ]
Saito, Akira [1 ]
Sato, Yoshihiro [1 ,2 ]
机构：
[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan
[2] ACT C Japan Sci & Technol Agcy JST, Kita Ku, Sapporo, Hokkaido 0600812, Japan
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 4卷 / 01期
关键词：
2+2+2] cycloaddition; alkynes; allenyl aldehydes; asymmetric synthesis; rhodium; METHYLENE-GAMMA-BUTYROLACTONES; ARYL ETHYNYL ETHERS; ARYLATIVE CYCLIZATION; CARBONYL-COMPOUNDS; AROMATIC-COMPOUNDS; RHODIUM; KETONES; CARBOCYCLIZATION; 1,6-ENYNES; 1,6-DIYNES;
D O I：
10.1002/ajoc.201402239
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Rhodium(I)-catalyzed cyclization of allenyl aldehydes with various alkynes was investigated. The cyclizations of internal alkynes that have both an electron-rich aromatic ring and an electron-withdrawing group at the terminus afforded [2+2+2] cycloaddition products in good yields with good to high regio- and enantioselectivity, while the reactions of terminal alkynes gave dienyl ketones instead of [2+2+2] cycloaddition products in good yields. These results indicate that the nature of the alkynes greatly influences the reaction course.
引用
收藏
页码：81 / 86
页数：6
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