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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DOIResolve DOI: http://doi.org/10.1039/c3cc48963a
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TypeArticle
Journal titleChemical Communications
ISSN1364-548X
Volume50
Issue26
Pages35053508; # of pages: 4
Subjectcarbohydrate derivative; cyclopropane derivative; furo[2,3 b]furan derivative; ketone derivative; pyran derivative; tin chloride; article; catalysis; chirality; cycloaddition; quantum yield; reaction analysis; stereochemistry; synthesis
AbstractStereospecific [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. © 2014 The Royal Society of Chemistry.
Publication date
LanguageEnglish
AffiliationNational Research Council Canada (NRC-CNRC); NRC Institute for Biological Sciences (IBS-ISB)
Peer reviewedYes
NPARC number21272121
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Record identifier378c7f56-4ff8-497f-832d-3a8e1593482d
Record created2014-07-23
Record modified2016-05-09
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