Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl3

Xiaofeng Ma; Qin Tang; Jun Ke; Jichao Zhang; Cong Wang; Haibo Wang; Yuxue Li; Huawu Shao

doi:10.1039/C3CC42292E

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Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl₃†

Xiaofeng Ma,^ac Qin Tang,^ac Jun Ke,^ac Jichao Zhang,^ac Cong Wang,^ac Haibo Wang,^ac Yuxue Li*^b and Huawu Shao*^a

Author affiliations

* Corresponding authors

^a Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, China
E-mail: shaohw@cib.ac.cn
Fax: +86-028-82890288

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
E-mail: liyuxue@sioc.ac.cn
Fax: +86-21-64166128

^c University of Chinese Academy of Sciences, China

Abstract

An effective and facile method for the synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives is described. The cyclization of 1,2-cyclopropanated sugars with olefins in the presence of BiCl₃ is highly diastereoselective. 2,2-Di-substituted cyclization products were obtained in good to excellent yields.

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Article information

DOI: https://doi.org/10.1039/C3CC42292E
Article type: Communication
Submitted: 29 Mar 2013
Accepted: 13 Jun 2013
First published: 13 Jun 2013

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Chem. Commun., 2013,49, 7085-7087

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Straightforward and highly diastereoselective synthesis of 2,2-di-substituted perhydrofuro[2,3-b]pyran (and furan) derivatives promoted by BiCl₃

X. Ma, Q. Tang, J. Ke, J. Zhang, C. Wang, H. Wang, Y. Li and H. Shao, Chem. Commun., 2013, 49, 7085 DOI: 10.1039/C3CC42292E

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