Synthesis of optically active dihydropyrans from asymmetric [4 + 2] cycloaddition of β,γ-unsaturated α-ketoesters with allenic esters
作者： Cheng-Kui Pei , Yu Jiang , Min Shi
DOI: 10.1039/C2OB25475A
关键词: Molecule 、 Cycloaddition 、 Stereoisomerism 、 Optically active 、 Chemistry 、 Dihydropyran 、 Catalysis 、 Organic chemistry
摘要: β-Isocupreidine (β-ICD) catalyzed asymmetric [4 + 2] cycloaddition of β,γ-unsaturated α-ketoesters with allenic esters afforded ester-substituted functionalized dihydropyran derivatives in high yields along enantioselectivities under mild conditions.
rsc.org
sci-hub.se 参考文章(94)
Yan Liu, Bingfeng Sun, Baomin Wang, Matthew Wakem, Li Deng, Catalytic asymmetric conjugate addition of simple alkyl thiols to alpha,beta-unsaturated N-acylated oxazolidin-2-ones with bifunctional catalysts. Journal of the American Chemical Society. ,vol. 131, pp. 418- 419 ,(2009) , 10.1021/JA8085092
Xiu-Chun Zhang, Shu-Hua Cao, Yin Wei, Min Shi, Phosphine-catalyzed highly diastereoselective [3+2] cyclization of isatin derived electron-deficient alkenes with α-allenic esters. Chemical Communications. ,vol. 47, pp. 1548- 1550 ,(2011) , 10.1039/C0CC04289G
Scott R. Gilbertson, Scott E. Collibee, Anton Agarkov, Asymmetric Catalysis with Libraries of Palladium β-Turn Phosphine Complexes Journal of the American Chemical Society. ,vol. 122, pp. 6522- 6523 ,(2000) , 10.1021/JA992306F
Larry Yet, Chemistry and biology of salicylihalamide a and related compounds. Chemical Reviews. ,vol. 103, pp. 4283- 4306 ,(2003) , 10.1021/CR030035S
Yingguang Zhu, Changwei Zhai, Yongli Yue, Liping Yang, Wenhao Hu, One-pot three-component tandem reaction of diazo compounds with anilines and unsaturated ketoesters: a novel synthesis of 2,3-dihydropyrrole derivatives. Chemical Communications. pp. 1362- 1364 ,(2009) , 10.1039/B822626A
Kap-Sun Yeung, Ian Paterson, Advances in the total synthesis of biologically important marine macrolides. Chemical Reviews. ,vol. 105, pp. 4237- 4313 ,(2005) , 10.1021/CR040614C
Arnaud Voituriez, Armen Panossian, Nicolas Fleury-Brégeot, Pascal Retailleau, Angela Marinetti, 2-Phospha[3]ferrocenophanes with planar chirality: synthesis and use in enantioselective organocatalytic [3 + 2] cyclizations. Journal of the American Chemical Society. ,vol. 130, pp. 14030- 14031 ,(2008) , 10.1021/JA806060A
Bryan J. Cowen, Scott J. Miller, Enantioselective [3 + 2]-Cycloadditions Catalyzed by a Protected, Multifunctional Phosphine-Containing α-Amino Acid Journal of the American Chemical Society. ,vol. 129, pp. 10988- 10989 ,(2007) , 10.1021/JA0734243
Gui-Ling Zhao, Jin-Wen Huang, Min Shi, Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one Organic Letters. ,vol. 5, pp. 4737- 4739 ,(2003) , 10.1021/OL0359416
Yuan-Qing Fang, Eric N. Jacobsen, Cooperative, highly enantioselective phosphinothiourea catalysis of imine-allene [3 + 2] cycloadditions. Journal of the American Chemical Society. ,vol. 130, pp. 5660- 5661 ,(2008) , 10.1021/JA801344W