Stereospecific [3+2] cycloaddition of 1,2-cyclopropanated sugars and ketones catalyzed by SnCl4: an efficient synthesis of multi-substituted perhydrofuro[2,3-b]furans and perhydrofuro[2,3-b]pyrans

Xiaofeng Ma; Jichao Zhang; Qin Tang; Jun Ke; Wei Zou; Huawu Shao

doi:10.1039/C3CC48963A

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Stereospecific [3+2] cycloaddition of 1,2-cyclopropanated sugars and ketones catalyzed by SnCl₄: an efficient synthesis of multi-substituted perhydrofuro[2,3-b]furans and perhydrofuro[2,3-b]pyrans†

Xiaofeng Ma,^a Jichao Zhang,^a Qin Tang,^a Jun Ke,^a Wei Zou^b and Huawu Shao*^a

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* 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 Institute for Biological Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario K1A 0R6, Canada

Abstract

Stereospecific [3+2] cycloaddition of 1,2-cyclopropanated sugars and ketones catalyzed by SnCl₄ is described. The method offers multi-substituted perhydrofuro[2,3-b]furans (bis-THFs) and perhydrofuro[2,3-b]pyrans containing a quaternary carbon chiral center in good to excellent yields.

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Article information

DOI: https://doi.org/10.1039/C3CC48963A
Article type: Communication
Submitted: 24 Nov 2013
Accepted: 06 Feb 2014
First published: 06 Feb 2014

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Chem. Commun., 2014,50, 3505-3508

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Stereospecific [3+2] cycloaddition of 1,2-cyclopropanated sugars and ketones catalyzed by SnCl₄: an efficient synthesis of multi-substituted perhydrofuro[2,3-b]furans and perhydrofuro[2,3-b]pyrans

X. Ma, J. Zhang, Q. Tang, J. Ke, W. Zou and H. Shao, Chem. Commun., 2014, 50, 3505 DOI: 10.1039/C3CC48963A

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