Chiral phosphoric acid-catalyzed highly enantioselective formal [3 + 2] cycloaddition reaction of azoalkenes with 3-vinylindoles has been established. Under mild conditions, the projected cycloaddition proceeded smoothly, affording a variety of 2,3-dihydropyrroles in high yields and excellent enantioselectivities, and also in a diastereospecific manner. As opposed to the common 4-atom synthons in the previous literature reports, azoalkenes served as 3-atom synthons. Besides, the observed selectivity was supported by primary theoretical calculation. The unique chemistry of azoalkenes disclosed herein will empower asymmetric synthesis of nitrogen-containing ring structural motifs in a broader context.
|Original language||English (US)|
|State||Published - Feb 17 2020|
Bibliographical noteKAUST Repository Item: Exported on 2020-10-01
Acknowledgements: Y.L. thanks the Singapore National Research Foundation, Prime Minister’s Office for the NRF Investigatorship Award (R-143-000-A15-281). Financial supports from the National University of Singapore (R-143-000-695-114 & C-141-000-092-001) and the National Natural Science Foundation of China (21672158 & 21702077) are also gratefully acknowledged.
FingerprintDive into the research topics of 'Catalytic Asymmetric Formal [3+2] Cycloaddition of Azoalkenes with 3-Vinylindoles: Synthesis of 2,3-Dihydropyrroles.'. Together they form a unique fingerprint.
CCDC 1957145: Experimental Crystal Structure Determination : ethyl 5-(5-cyano-1H-indol-3-yl)-1-[(methoxycarbonyl)amino]-2-methyl-4-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylate
Mei, G. (Creator), Zheng, W. (Creator), Gonçalves, T. P. (Creator), Tang, X. (Creator), Huang, K. (Creator), Lu, Y. (Creator), Mei, G. (Creator), Zheng, W. (Creator), Gonçalves, T. P. (Creator), Tang, X. (Creator) & Lu, Y. (Creator), Cambridge Crystallographic Data Centre, Feb 7 2020
DOI: 10.5517/ccdc.csd.cc23pkq3, http://hdl.handle.net/10754/664854