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Synlett 2010(11): 1609-1616  
DOI: 10.1055/s-0029-1258085
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Rapid Synthesis of 2-Aryl Polyhydroxylated Pyrrolidines

Jia-Kun Sua,b, Yue-Mei Jiaa, Ruirui Hec, Pei-Xin Ruia, Nanyin Hanc, Xihui Hec, Junfeng Xianga, Xin Chenc, Jinghua Zhuc, Chu-Yi Yu*a
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China
Fax: +86(10)82616433; e-Mail: yucy@iccas.ac.cn;
b Graduate University of Chinese Academy of Sciences, Beijing 100049, P. R. of China
c School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. of China
Further Information

Publication History

Received 7 April 2010
Publication Date:
11 June 2010 (online)

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Abstract

Friedel-Crafts-type reaction of electron-rich aromatic compounds with polyhydroxylated cyclic nitrones catalyzed by Brønsted acid afforded 2-aryl polyhydroxylated pyrrolidines in good to excellent yields with high diastereoselectivity under mild conditions.

Key words

2-aryl polyhydroxylated pyrrolidines - iminosugars - Brønsted acid - polyhydroxylated cyclic nitrones - Friedel-Crafts ­reaction

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12

The crystal structures of 19b and 26 have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition numbers CCDC 756237 and 756238, respectively.