Solvent-Controlled Switchable Domino Reactions of MBH Carbonate: Synthesis of Benzothiophene Fused α-Pyran, 2,3-Dihydrooxepine, and Oxatricyclodecene Derivatives.
作者： Jiru Jia , Aimin Yu , Shanshan Ma , Youquan Zhang , Ke Li
DOI: 10.1021/ACS.ORGLETT.7B02916
关键词: Carbonate 、 Solvent 、 Pyran 、 Benzothiophene 、 Broad spectrum 、 Domino 、 Regioselectivity 、 Organic chemistry 、 Chemistry
摘要: Solvent-controlled switchable domino reactions between 2-alkylidenebenzothiophene-3(2H)-ones and Morita–Baylis–Hillamn (MBH) carbonate were developed. All exhibited excellent regioselectivity, producing a broad spectrum of benzothiophene-fused α-pyran, 2,3-dihydrooxepine, oxatricyclodecene derivatives. Furthermore, [4 + 2], 3], related from identical substrates can be controlled.
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crystallography.net参考文章(38)
Yufen Liu, Yanlong Du, Aimin Yu, Dabin Qin, Xiangtai Meng, Diverse synthesis of pyrano[2,3-b]indol and dihydropyrano[2,3-b]indol via tunable Lewis bases catalyzed domino reactions Tetrahedron. ,vol. 71, pp. 7706- 7716 ,(2015) , 10.1016/J.TET.2015.07.057
Peizhong Xie, You Huang, Morita–Baylis–Hillman adduct derivatives (MBHADs): versatile reactivity in Lewis base-promoted annulation Org. Biomol. Chem.. ,vol. 13, pp. 8578- 8595 ,(2015) , 10.1039/C5OB00865D
Yufen Liu, Qi Zhang, Yanlong Du, Aimin Yu, Kui Zhang, Xiangtai Meng, Convenient synthesis of substituted tetrahydrofuran via Lewis base catalyzed [3 + 2] domino reactions RSC Advances. ,vol. 4, pp. 52629- 52632 ,(2014) , 10.1039/C4RA09249J
Yuanzhi Xia, Yong Liang, Yuanyuan Chen, Ming Wang, Lei Jiao, Feng Huang, Song Liu, Yahong Li, Zhi-Xiang Yu, An unexpected role of a trace amount of water in catalyzing proton transfer in phosphine-catalyzed (3 + 2) cycloaddition of allenoates and alkenes. Journal of the American Chemical Society. ,vol. 129, pp. 3470- 3471 ,(2007) , 10.1021/JA068215H
Qiongmei Zhang, Lei Yang, Xiaofeng Tong, 2-(Acetoxymethyl)buta-2,3-dienoate, a versatile 1,4-biselectrophile for phosphine-catalyzed (4 + n) annulations with 1,n-Bisnucleophiles (n = 1, 2). Journal of the American Chemical Society. ,vol. 132, pp. 2550- 2551 ,(2010) , 10.1021/JA100432M
Amaresh Mishra, Chang-Qi Ma, Peter Bäuerle, Functional oligothiophenes: molecular design for multidimensional nanoarchitectures and their applications. Chemical Reviews. ,vol. 109, pp. 1141- 1276 ,(2009) , 10.1021/CR8004229
Rong Zhou, Jianfang Wang, Haibin Song, Zhengjie He, Phosphine-catalyzed cascade [3 + 2] cyclization-allylic alkylation, [2 + 2 + 1] annulation, and [3 + 2] cyclization reactions between allylic carbonates and enones. Organic Letters. ,vol. 13, pp. 580- 583 ,(2011) , 10.1021/OL102738B
Qi-Lin Wang, Lin Peng, Fei-Ying Wang, Ming-Liang Zhang, Li-Na Jia, Fang Tian, Xiao-Ying Xu, Li-Xin Wang, An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles. Chemical Communications. ,vol. 49, pp. 9422- 9424 ,(2013) , 10.1039/C3CC45139A
Yiting Gu, Pengfei Hu, Chunjie Ni, Xiaofeng Tong, Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β′-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine Journal of the American Chemical Society. ,vol. 137, pp. 6400- 6406 ,(2015) , 10.1021/JACS.5B03273
Xiaoyu Han, Weijun Yao, Tianli Wang, Yong Ren Tan, Ziyu Yan, Jacek Kwiatkowski, Yixin Lu, Asymmetric Synthesis of Spiropyrazolones through Phosphine‐Catalyzed [4+1] Annulation Angewandte Chemie. ,vol. 53, pp. 5643- 5647 ,(2014) , 10.1002/ANIE.201311214