Rhodium-Catalyzed [3+2+2] and [2+2+2] Cycloadditions of Two Alkynes with Cyclopropylideneacetamides

被引：51
作者：
Yoshida, Tomoka [1 ]
Tajima, Yuki [1 ]
Kobayashi, Masayuki [1 ]
Masutomi, Koji [2 ]
Noguchi, Keiichi [3 ]
Tanaka, Ken [1 ,2 ,4 ]
机构：
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528550, Japan
[3] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
[4] Japan Sci & Technol Agcy JST, ACT C, Kawaguchi, Saitama 3320012, Japan
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 28期
基金：
日本科学技术振兴机构;
关键词：
asymmetric catalysis; cycloaddition; heterocycles; rhodium; synthetic methods; REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION; ETHYL CYCLOPROPYLIDENEACETATE; (3+2)+2 CARBOCYCLIZATION; COCYCLIZATION; REACTIVITY; ALKENYLIDENECYCLOPROPANES; ALKYLIDENECYCLOPROPANES; CONSTRUCTION; COMPLEXES; REGIO;
D O I：
10.1002/anie.201502505
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
It has been established that a cationic rhodium(I)/H-8-binap complex catalyzes the [3+2+2] cycloaddition of 1,6-diynes with cyclopropylideneacetamides to produce cycloheptadiene derivatives through cleavage of cyclopropane rings. In contrast, a cationic rhodium(I)/(S)-binap complex catalyzes the enantioselective [2+2+2] cycloaddition of terminal alkynes, acetylenedicarboxylates, and cyclopropylideneacetamides to produce spiro-cyclohexadiene derivatives which retain the cyclopropane rings.
引用
收藏
页码：8241 / 8244
页数：4
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