FeCl3-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect

Jiajia Cheng; Xinjun Tang; Yihua Yu; Shengming Ma

doi:10.1039/C2CC36941A

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FeCl₃-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect†

Jiajia Cheng,^a Xinjun Tang,^a Yihua Yu^b and Shengming Ma*^ac

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* Corresponding authors

^a State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: masm@sioc.ac.cn
Fax: (+86)-21-6260-9305

^b Shanghai Key Laboratory of Magnetic Resonance, Department of Physics, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. China

^c Shanghai Key Laboratory of Green Chemistry and Chemical Process, Department of Chemistry, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P.R. China

Abstract

FeCl₃-catalyzed aza-Prins-cyclization reaction of α-sulfonamido-allenes with aldehydes afforded 1,2,3,6-tetrahydropyridine or 2,5-dihydro-1H-pyrrole derivatives efficiently and highly selectively. The different regioselectivity is probably caused by the stabilizing effect of the phenyl group on the positively charged allylic intermediate.

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Article information

DOI: https://doi.org/10.1039/C2CC36941A
Article type: Communication
Submitted: 25 Sep 2012
Accepted: 19 Oct 2012
First published: 22 Oct 2012

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Chem. Commun., 2012,48, 12074-12076

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FeCl₃-catalyzed cyclization of α-sulfonamido-allenes with aldehydes—the substituent effect

J. Cheng, X. Tang, Y. Yu and S. Ma, Chem. Commun., 2012, 48, 12074 DOI: 10.1039/C2CC36941A

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