Dithiane Induced Cycloaddition/Aromatization Tactic for the Synthesis of Multisubstituted Furans
作者： Junshan Lai , Yongping Liang , Teng Liu , Shouchu Tang
DOI: 10.1021/ACS.ORGLETT.6B00699
关键词: Dithiane 、 Allene 、 Chemistry 、 Cycloaddition 、 Organic chemistry 、 Aromatization
摘要: The development of a new transition-metal-free tactic for convergent, one-pot synthesis multisubstituted furans by β-chloro-vinyl dithiane cyclization with aldehydes is described. Key to the success was vinylidene site as donor allene that generates active dihydrofuran, which undergoes in situ aromatization under mild conditions.
acs.org
sci-hub.se 参考文章(48)
Niels H. Andersen, Alan D. Denniston, David A. McCrae, Dithiane chemistry. 5. Silyl and lithio derivatives of a propynal dithioacetal Journal of Organic Chemistry. ,vol. 13, pp. 1145- 1146 ,(1982) , 10.1021/JO00345A055
Brian A. Keay, Synthesis of multi-substituted furan rings: the role of silicon Chemical Society Reviews. ,vol. 28, pp. 209- 215 ,(1999) , 10.1039/A809439J
Joshua R. Hummel, Jonathan A. Ellman, Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades. Journal of the American Chemical Society. ,vol. 137, pp. 490- 498 ,(2015) , 10.1021/JA5116452
Shengming Ma, Electrophilic Addition and Cyclization Reactions of Allenes Accounts of Chemical Research. ,vol. 42, pp. 1679- 1688 ,(2009) , 10.1021/AR900153R
Renji Okazaki, Yoshio Negishi, Naoki Inamoto, A new simple synthesis of variously substituted furans and butenolides Journal of The Chemical Society, Chemical Communications. pp. 1055- 1056 ,(1982) , 10.1039/C39820001055
Viola Breker, Hülya Sak, Giusy Baracchi-Krause, Norbert Krause, Synthesis and properties of a biotin-tagged NHC–gold complex Tetrahedron Letters. ,vol. 56, pp. 3390- 3392 ,(2015) , 10.1016/J.TETLET.2015.01.023
Miguel Yus, Carmen Nájera, Francisco Foubelo, The role of 1,3-dithianes in natural product synthesis Tetrahedron. ,vol. 59, pp. 6147- 6212 ,(2003) , 10.1016/S0040-4020(03)00955-4
Rick L. Danheiser, Eric J. Stoner, Hiroo Koyama, Dennis S. Yamashita, Carrie A. Klade, A new synthesis of substituted furans Journal of the American Chemical Society. ,vol. 111, pp. 4407- 4413 ,(1989) , 10.1021/JA00194A040
Wenbin Du, Lixia Tian, Junshan Lai, Xing Huo, Xingang Xie, Xuegong She, Shouchu Tang, Iron-catalyzed radical oxidative coupling reaction of aryl olefins with 1,3-dithiane. Organic Letters. ,vol. 16, pp. 2470- 2473 ,(2014) , 10.1021/OL500850D
Yizhou Dong, Qian Shi, Yi-Nan Liu, Xiang Wang, Kenneth F. Bastow, Kuo-Hsiung Lee, Antitumor agents. 266. Design, synthesis, and biological evaluation of novel 2-(furan-2-yl)naphthalen-1-ol derivatives as potent and selective antibreast cancer agents. Journal of Medicinal Chemistry. ,vol. 52, pp. 3586- 3590 ,(2009) , 10.1021/JM9001567