Issue 4, 2011
From the journal:

Chemical Communications

Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles viapyridine catalyzed formal [4+1] annulation†

Chun-Rong Liu,a   Ben-Hu Zhu,c   Jun-Cheng Zheng,a   Xiu-Li Sun,a   Zuowei Xieb  and  Yong Tang*a  

* Corresponding authors

a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China
E-mail: tangy@mail.sioc.ac.cn

b Department of Chemistry, The Chinese University of Hong Kong, Shatin, New Territories, Hong Kong, China

c School of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123, China

Abstract

A pyridine-catalyzed ylide cyclization affording dihydrofurans and dihydropyrroles has been developed. In the presence of a catalytic amount of pyridine and Fe(Tcpp)Cl, α-ylidene-β-diketones and α,β-unsaturated imines react with diazoacetates providing dihydrofurans and dihydropyrroles respectively, in up to 96% yield with high diastereoselectivities.

Graphical abstract: Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles viapyridine catalyzed formal [4+1] annulation

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Article information

DOI
https://doi.org/10.1039/C0CC02347G
Article type
Communication
Submitted
03 Jul 2010
Accepted
13 Oct 2010
First published
17 Nov 2010

Chem. Commun., 2011,47, 1342-1344

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Highly diastereroselective synthesis of dihydrofurans and dihydropyrroles viapyridine catalyzed formal [4+1] annulation

C. Liu, B. Zhu, J. Zheng, X. Sun, Z. Xie and Y. Tang, Chem. Commun., 2011, 47, 1342 DOI: 10.1039/C0CC02347G

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