Rhodium-catalyzed arylative cyclization of alkynones induced by addition of arylboronic acids

被引：38
作者：
Miura, Tomoya [1 ]
Shimada, Masahiko [1 ]
Murakami, Masahiro [1 ]
机构：
[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6158510, Japan
来源：
TETRAHEDRON | 2007年 / 63卷 / 27期
基金：
日本学术振兴会;
关键词：
D O I：
10.1016/j.tet.2007.03.025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Alkynones react with arylboronic acids in the presence of a rhodium(I) catalyst to afford four- and five-membered-ring cyclic alcohols equipped with a tetrasubstituted exocyclic olefin. The cyclic allylic alcohol skeleton is constructed by the carbon-carbon bond formation between the carbonyl group and an alkenylrhodium(I) intermediate formed by the regioselective addition of an arylrhodium(I) species across the carbon-carbon triple bond. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6131 / 6140
页数：10
相关论文
共 50 条
[21]   Highly enantioselective rhodium-catalyzed conjugate addition of arylboronic acids to enones at room temperature [J].
Martina, SLX ;
Minnaard, AJ ;
Hessen, B ;
Feringa, BL .
TETRAHEDRON LETTERS, 2005, 46 (42) :7159-7163
[22]   Rhodium-catalyzed addition of arylboronic acids to alkynyl aza-heteroaromatic compounds in water [J].
Lautens, M ;
Yoshida, M .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :762-769
[23]   Chiral Pyrrolidines and Piperidines from Enantioselective Rhodium-Catalyzed Cascade Arylative Cyclization [J].
Serpier, Fabien ;
Flamme, Benjamin ;
Brayer, Jean-Louis ;
Folleas, Benoit ;
Darses, Sylvain .
ORGANIC LETTERS, 2015, 17 (07) :1720-1723
[24]   Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration [J].
O'Brien, Luke ;
Karad, Somnath Narayan ;
Lewis, William ;
Lam, Hon Wai .
CHEMICAL COMMUNICATIONS, 2019, 55 (76) :11366-11369
[25]   Rhodium-catalyzed tandem addition-cyclization-rearrangement of alkynylhydrazones with organoboronic acids [J].
Choi, Kyoungmin ;
Park, Hoyoon ;
Lee, Chulbom .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
[26]   Rhodium-Catalyzed Tandem Addition-Cyclization-Rearrangement of Alkynylhydrazones with Organoboronic Acids [J].
Choi, Kyoungmin ;
Park, Hoyoon ;
Lee, Chulbom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (33) :10407-10411
[27]   Rhodium-Catalyzed Tandem Addition-Cyclization-Rearrangement of Alkynylhydrazones with Organoboronic Acids [J].
Lee, Chulbom (chulbom@snu.ac.kr), 2018, American Chemical Society (140)
[28]   Enantioselective rhodium-catalyzed addition of arylboronic acids to N-heteroaryl ketones: synthesis of α-hydroxy acids [J].
Zhu, Jinbin ;
Li, Zhenyue ;
Li, Jiaqi ;
Tian, Duanshuai ;
Xu, Ronghua ;
Tan, Zhiyong ;
Chen, Zhengwang ;
Tang, Wenjun .
CHEMICAL SCIENCE, 2023, 14 (06) :1606-1612
[29]   Rhodium-catalyzed arylative and alkenylative cyclization of 1,5-enynes induced by geminal carbometalation of alkynes [J].
Chen, Yiyun ;
Lee, Chulbom .
Journal of the American Chemical Society, 2006, 128 (49) :15598-15599
[30]   Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Nitroolefins: Formal Synthesis of (S)-SKF 38393 [J].
Huang, Kung-Chih ;
Gopula, Balraj ;
Kuo, Ting-Shen ;
Chiang, Chien-Wei ;
Wu, Ping-Yu ;
Henschke, Julian P. ;
Wu, Hsyueh-Liang .
ORGANIC LETTERS, 2013, 15 (22) :5730-5733
12345