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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,Jichao Zhang,Qin Tang,Jun Ke,Wei Zou,Huawu Shao
Chemical Communications Pub Date : 02/06/2014 00:00:00 , DOI:10.1039/C3CC48963A
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.

Graphical abstract: 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
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