Rhodium-catalysed cyclisation reaction of allenynes with arylboronic acids

作者: Tomoya Miura , Keita Ueda , Yusuke Takahashi , Masahiro Murakami

DOI: 10.1039/B810665G

关键词: Organic chemistryMalonateCatalysisBicyclic moleculeRhodiumStereoselectivityChemistry

摘要: Allenynes having malonate-based tethers reacted with arylboronic acids in the presence of a rhodium(I) catalyst to sequentially form three carbon–carbon bonds, and arylated bicyclic skeletons were constructed stereoselective manner.

参考文章(28)
Masahiko Shimada, Tatsuro Harumashi, Tomoya Miura, Masahiro Murakami, Rhodium-catalyzed cyclization reaction of 1,6-enynes with arylboronic acids through beta-hydride elimination/hydrorhodation sequence Chemistry-an Asian Journal. ,vol. 3, pp. 1035- 1040 ,(2008) , 10.1002/ASIA.200700407
Tomoya Miura, Masahiko Shimada, Masahiro Murakami, Rhodium-catalyzed arylative cyclization of alkynones induced by addition of arylboronic acids Tetrahedron. ,vol. 63, pp. 6131- 6140 ,(2007) , 10.1016/J.TET.2007.03.025
Tomoya Miura, Taisuke Sasaki, Hiroki Nakazawa, Masahiro Murakami, Ketone Synthesis by Intramolecular Acylation of Organorhodium(I) with Ester Journal of the American Chemical Society. ,vol. 127, pp. 1390- 1391 ,(2005) , 10.1021/JA043123I
Paul Ha-Yeon Cheong, Philip Morganelli, Michael R. Luzung, K. N. Houk, F. Dean Toste, Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction. Journal of the American Chemical Society. ,vol. 130, pp. 4517- 4526 ,(2008) , 10.1021/JA711058F
Takahiro Nishimura, Sho Hirabayashi, Yuichi Yasuhara, Tamio Hayashi, Rhodium-catalyzed asymmetric hydroarylation of diphenylphosphinylallenes with arylboronic acids. Journal of the American Chemical Society. ,vol. 128, pp. 2556- 2557 ,(2006) , 10.1021/JA058763F
Toshiyuki Hirose, Naoki Miyakoshi, Chisato Mukai, Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction Journal of Organic Chemistry. ,vol. 73, pp. 1061- 1066 ,(2008) , 10.1021/JO702330Y
Yiyun Chen, Chulbom Lee, Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes. Journal of the American Chemical Society. ,vol. 128, pp. 15598- 15599 ,(2006) , 10.1021/JA067125+
Ryo Shintani, Kazuhiro Okamoto, Yusuke Otomaru, Kazuhito Ueyama, Tamio Hayashi, Catalytic Asymmetric Arylative Cyclization of Alkynals: Phosphine-Free Rhodium/Diene Complexes as Efficient Catalysts Journal of the American Chemical Society. ,vol. 127, pp. 54- 55 ,(2005) , 10.1021/JA044021V
Tomoya Miura, Tatsuro Harumashi, Masahiro Murakami, Cyclization Reaction of Cyano-Substituted Unsaturated Esters Prompted by Conjugate Addition of Organoborons Organic Letters. ,vol. 9, pp. 741- 743 ,(2007) , 10.1021/OL062882Y