An organocatalytic asymmetric sequential allylic alkylation-cyclization of Morita-Baylis-Hillman carbonates and 3-hydroxyoxindoles.
作者： Qi-Lin Wang , Lin Peng , Fei-Ying Wang , Ming-Liang Zhang , Li-Na Jia
DOI: 10.1039/C3CC45139A
关键词:
摘要: The first organocatalytic asymmetric sequential allylic alkylation–cyclization of Morita–Baylis–Hillman carbonates and 3-hydroxyoxindoles has been developed to afford spirooxindoles bearing α-methylene-γ-butyrolactone motifs in 25–85% yield, 60–94% ee up >20 : 1 diastereoselectivity.
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sci-hub.se 参考文章(43)
Qiang Wei, Liu-Zhu Gong, Organocatalytic Asymmetric Formal [4 + 2] Cycloaddition for the Synthesis of Spiro[4-cyclohexanone-1,3′-oxindoline] Derivatives in High Optical Purity Organic Letters. ,vol. 12, pp. 1008- 1011 ,(2010) , 10.1021/OL100020V
Yun-Long Guo, Jian-Fei Bai, Lin Peng, Liang-Liang Wang, Li-Na Jia, Xi-Ya Luo, Fang Tian, Xiao-Ying Xu, Li-Xin Wang, Direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(5H)-one with aldimine catalyzed by quinine. Journal of Organic Chemistry. ,vol. 77, pp. 8338- 8343 ,(2012) , 10.1021/JO301115T
T. Patrick Montgomery, Abbas Hassan, Boyoung Y. Park, Michael J. Krische, Enantioselective conversion of primary alcohols to α-exo-methylene γ-butyrolactones via iridium-catalyzed C-C bond-forming transfer hydrogenation: 2-(alkoxycarbonyl)allylation. Journal of the American Chemical Society. ,vol. 134, pp. 11100- 11103 ,(2012) , 10.1021/JA303839H
P. Buchwald, N. Bodor, Computer-aided drug design: the role of quantitative structure-property, structure-activity and structure-metabolism relationships (QSPR, QSAR, QSMR) Drugs of The Future. ,vol. 27, pp. 577- 588 ,(2002) , 10.1358/DOF.2002.027.06.856934
Yankai Liu, Manuel Nappi, Elena Arceo, Silvia Vera, Paolo Melchiorre, Asymmetric catalysis of Diels-Alder reactions with in situ generated heterocyclic ortho-quinodimethanes. Journal of the American Chemical Society. ,vol. 133, pp. 15212- 15218 ,(2011) , 10.1021/JA206517S
Christiane Marti, Erick M. Carreira, Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole Alkaloids European Journal of Organic Chemistry. ,vol. 2003, pp. 2209- 2219 ,(2003) , 10.1002/EJOC.200300050
Michele Retini, Giulia Bergonzini, Paolo Melchiorre, Dioxindole in asymmetric catalytic synthesis: direct access to 3-substituted 3-hydroxy-2-oxindoles via 1,4-additions to nitroalkenes. Chemical Communications. ,vol. 48, pp. 3336- 3338 ,(2012) , 10.1039/C2CC30198A
Bin Tan, Nuno R. Candeias, Carlos F. Barbas, Construction of bispirooxindoles containing three quaternary stereocentres in a cascade using a single multifunctional organocatalyst Nature Chemistry. ,vol. 3, pp. 473- 477 ,(2011) , 10.1038/NCHEM.1039
Xavier Companyó, Andrea Mazzanti, Albert Moyano, Anna Janecka, Ramon Rios, First one-pot organocatalytic synthesis of α-methylene-γ-lactones Chemical Communications. ,vol. 49, pp. 1184- 1186 ,(2013) , 10.1039/C2CC38659C
Liang-Liang Wang, Lin Peng, Jian-Fei Bai, Qing-Chun Huang, Xiao-Ying Xu, Li-Xin Wang, Highly organocatalytic asymmetric Michael–ketone aldol–dehydration domino reaction: straightforward approach to construct six-membered spirocyclic oxindoles Chemical Communications. ,vol. 46, pp. 8064- 8066 ,(2010) , 10.1039/C0CC03032E