Synthesis 2017; 49(18): 4292-4298
DOI: 10.1055/s-0036-1588876
special topic
© Georg Thieme Verlag Stuttgart · New York

Facile Construction of Pyrrolo[1,2-a]indolenine Scaffold via Dia­stereoselective [3+2] Annulation of Donor–Acceptor Cyclopropane with Indolenine

Jie Li
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China   eMail: hyangchem@csu.edu.cn
,
Jun-An Xiao
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China   eMail: hyangchem@csu.edu.cn
,
Shu-Juan Zhao
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China   eMail: hyangchem@csu.edu.cn
,
Hao-Yue Xiang
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China   eMail: hyangchem@csu.edu.cn
,
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. of China   eMail: hyangchem@csu.edu.cn
› Institutsangaben
We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21576296) and Central South University.
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Publikationsverlauf

Received: 11. April 2017

Accepted after revision: 15. Mai 2017

Publikationsdatum:
19. Juli 2017 (online)

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

A novel synthetic protocol for the assembly of pyrrolo[1,2-a]indolenine has been developed through a highly diastereoselective [3+2] annulation of 1,1-cyclopropanediesters with indolenines in the presence of catalytic Yb(OTf)3. This new strategy allows a facile construction of the multicyclic system with the flexible variation on the substituents in high yields (up to 86%) with excellent diastereoselectivities (>20:1 dr) in most cases.

Supporting Information

 
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