Hetero [6+3] cycloaddition of fulvenes with N-alkylidene glycine esters: a facile synthesis of the delavayine and incarvillateine framework

Bor-Cherng Hong; Arun Kumar Gupta; Ming-Fun Wu; Ju-Hsiou Liao; Gene-Hsiang Lee

doi:10.1021/ol034329b

Hetero [6+3] cycloaddition of fulvenes with N-alkylidene glycine esters: a facile synthesis of the delavayine and incarvillateine framework

Org Lett. 2003 May 15;5(10):1689-92. doi: 10.1021/ol034329b.

Authors

Bor-Cherng Hong¹, Arun Kumar Gupta, Ming-Fun Wu, Ju-Hsiou Liao, Gene-Hsiang Lee

Affiliation

¹ Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, R.O.C. chebch@ccunix.ccu.edu.tw

PMID: 12735753
DOI: 10.1021/ol034329b

Abstract

[reaction: see text] In contrast to the [3+2] or [4+3] cycloaddition of N-metalated azomethine ylides and various alkenes, N-benzylidene glycine ethyl ester reacts with fulvenes to give the hetero [6+3] cycloaddition adducts with high stereoselectivity, constituting an efficient and novel route to [2]pyrindines.