Synthesis 2019; 51(06): 1353-1364
DOI: 10.1055/s-0037-1610848
paper
© Georg Thieme Verlag Stuttgart · New York

4-(N,N-Dimethylamino)pyridine (DMAP)-Catalyzed 1,3-Dipolar Cycloaddition of 3-Aminooxindole-Based Azomethine Ylides with α,β-Unsaturated Acyl Phosphonates for the Construction of Spiropyrrolidinyl-2,3′-oxindoles

Jin He
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
,
Rong-Guo Sun
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
,
Li Fan
b  Library, Guizhou Normal University, Guiyang 550001, P. R. of China
,
Shi-Yan Tian
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
,
Ting-Ping Huang
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
,
Zhuo Chen*
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
,
a  School of Chemistry and Materials Science, Guizhou Normal University, Guiyang 550001, P. R. of China   Email: chenzhuo19@163.com   Email: chenlin8310@aliyun.com
› Author Affiliations
We thank the National Natural Science Foundation of China (21762013), the Science and Technology Project of Guizhou Province (Qian Ke He LH Zi [2016] 7220, Qian Ke He SY Zi [2015] 3014 and Qian Ke He Ping Tai Ren Cai [2017] 5726), the Science and Technology Development Project of Education Department of Guizhou Province for Young Talents (Qian Jiao He KY Zi [2016] 133), the Doctoral Research Funds of Guizhou Normal University (2015) and the Innovation and Entrepreneurship Project of Guizhou Province for Undergraduates (2018520167) for generous financial support.
Further Information

Publication History

Received: 03 September 2018

Accepted after revision: 21 October 2018

Publication Date:
27 November 2018 (eFirst)

Abstract

A novel, one-pot 1,3-dipolar cycloaddition of 3-amimooxindole-based azomethine ylides with α,β-unsaturated acyl phosphonates and subsequent derivatization of the intermediates is described. Employing 4-(N,N-dimethylamino)pyridine (DMAP), an organic Brønsted base, as a robust catalyst leads to an architecturally diverse set of spiropyrrolidinyl-2,3′-oxindoles bearing four contiguous stereocenters and an ester or an amide at the γ-position of the pyrrolidine motif. The products are obtained in moderate to excellent yields and with good diastereoselectivities under mild conditions. The potential of this methodology is demonstrated through a gram-scale reaction and a further transformation of one of the products.

Supporting Information

 
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