Rh(I)-catalyzed Pauson-Khand reaction and cycloisomerization of allenynes: selective preparation of monocyclic, bicyclo[m.3.0], and bicyclo[5.2.0] ring systems |
| |
Authors: | Mukai Chisato Inagaki Fuyuhiko Yoshida Tatsunori Yoshitani Katsuya Hara Yasuyuki Kitagaki Shinji |
| |
Institution: | Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. cmukai@kenroku.kanazawa-u.ac.jp |
| |
Abstract: | reaction: see text] Rhodium(I)-catalyzed PKR of allenynes was found to be applicable for constructing azabicyclo5.3.0]decadienone as well as oxabicyclo5.3.0]decadienone frameworks. In addition, a reliable procedure for constructing a 10-monosubstituted bicyclo5.3.0]deca-1,7-dien-9-one ring system by the rhodium(I)-catalyzed PKR of allenynes was developed under the condition of 10 atm of CO. Investigation of the rhodium(I)-catalyzed cycloisomerization of 4-phenylsulfonylnona-2,3-dien-8-ynes under nitrogen atmosphere gave the corresponding cyclohexene derivatives, whereas the C1-homologated allenynes produced cycloheptene derivatives and/or bicyclo5.2.0]nonene skeletons depending on the substitution pattern at the allenic terminus. Thus, proper choice of the starting allenynes and reaction conditions led to the selective formation of 2-phenylsulfonylbicyclo5.3.0]deca-1,7-dien-9-ones (Pauson-Khand-type product), 3-alkylidene-1-phenylsulfonyl-2-vinylcycloheptene derivatives, and bicyclo5.2.0]nonene frameworks. |
| |
Keywords: | |
本文献已被 PubMed 等数据库收录! |
|