Alkylidene Meldrum's Acids as Platforms for the Vinylogous Synthesis of Dihydropyranones
作者： Sylvain Oudeyer , Vincent Gandon , Vincent Gandon , Martial Toffano , Jean-François Brière
关键词:
摘要: Upon Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids proved to be competent vinylogous platforms able undergo a formal (4+2) cycloaddition reaction with dihydro-2,3-furandione, providing an unprecedented route 3,6-dihydropyran-2-ones as spiro[4.5]decane derivatives up 98 % ee thanks the commercially available Takemoto catalyst. Preliminary investigation showed that this could extended other activated ketones, establishing these novel C4-synthon in series.
sci-hub.st 参考文章(42)
J. Leitich, P. Schuster, A. Eitel, Zur acidita¨t cyclischer acylale substituierter methylenmalonsa¨uren: Eine klasse von ambidenten sa¨uren Zur Kenntnis cylischer Acylale 15. Mitt. Tetrahedron. ,vol. 23, pp. 2221- 2227 ,(1967) , 10.1016/0040-4020(67)80057-7
Youqiang Lin, Limin Yang, Yue Deng, Guofu Zhong, Cooperative catalysis of N-heterocyclic carbene and Brønsted acid for a highly enantioselective route to unprotected spiro-indoline-pyrans. Chemical Communications. ,vol. 51, pp. 8330- 8333 ,(2015) , 10.1039/C5CC02096D
P. Schuster, A. Stephen, O. E. Polansky, F. Wessely, Messung der Aciditätskonstanten einiger elektrisch neutraler organischer Lewissäuren Monatshefte Fur Chemie. ,vol. 99, pp. 1246- 1276 ,(1968) , 10.1007/BF00913786
Scott E. Denmark, John R. Heemstra, Gregory L. Beutner, Catalytic, Enantioselective, Vinylogous Aldol Reactions Angewandte Chemie. ,vol. 44, pp. 4682- 4698 ,(2005) , 10.1002/ANIE.200462338
Thomas B Poulsen, Carlos Alemparte, Karl Anker Jørgensen, None, Enantioselective Organocatalytic Allylic Amination Journal of the American Chemical Society. ,vol. 127, pp. 11614- 11615 ,(2005) , 10.1021/JA0539847
Giovanni Casiraghi, Lucia Battistini, Claudio Curti, Gloria Rassu, Franca Zanardi, The Vinylogous Aldol and Related Addition Reactions: Ten Years of Progress† Chemical Reviews. ,vol. 111, pp. 3076- 3154 ,(2011) , 10.1021/CR100304N
Tian-Ze Li, Yu Jiang, Yu-Qing Guan, Feng Sha, Xin-Yan Wu, Direct enantioselective vinylogous aldol–cyclization cascade reaction of allyl pyrazoleamides with isatins: asymmetric construction of spirocyclic oxindole–dihydropyranones Chemical Communications. ,vol. 50, pp. 10790- 10792 ,(2014) , 10.1039/C4CC04235B
Zhaoxin Xiao, Chenxia Yu, Tuanjie Li, Xiang-Shan Wang, Changsheng Yao, N-Heterocyclic Carbene/Lewis Acid Strategy for the Stereoselective Synthesis of Spirocyclic Oxindole–Dihydropyranones Organic Letters. ,vol. 16, pp. 3632- 3635 ,(2014) , 10.1021/OL501224P
Paolo S. Tiseni, René Peters, Katalytische asymmetrische Synthese von δ‐Lactonen durch [4+2]‐Cycloaddition von zwitterionischen Dienolaten, erzeugt aus α,β‐ungesättigten Säurechloriden Angewandte Chemie. ,vol. 119, pp. 5419- 5422 ,(2007) , 10.1002/ANGE.200700859
Li-Tao Shen, Pan-Lin Shao, Song Ye, N-Heterocyclic Carbene-Catalyzed Cyclization of Unsaturated Acyl Chlorides and Ketones Advanced Synthesis & Catalysis. ,vol. 353, pp. 1943- 1948 ,(2011) , 10.1002/ADSC.201100178