10.1021/ol400735z.s002 Stephen G. Davies Stephen G. Davies Aude L. A. Figuccia Aude L. A. Figuccia Ai M. Fletcher Ai M. Fletcher Paul M. Roberts Paul M. Roberts James E. Thomson James E. Thomson Asymmetric Syntheses of (−)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin via a Ring-Expansion Approach American Chemical Society 2016 iodoamination Deoxyallonojirimycin epimeric bishomoallylic amines diastereoisomer iodomethylpyrrolidine 7.4 ApproachThe Asymmetric Syntheses Deoxymannojirimycin deoxyallonojirimycin cyclic carbonates deoxymannojirimycin Subsequent deprotection material synthese dr diastereoisomerically 2016-02-19 11:30:47 Journal contribution https://acs.figshare.com/articles/journal_contribution/Asymmetric_Syntheses_of_1_Deoxymannojirimycin_and_1_Deoxyallonojirimycin_via_a_Ring_Expansion_Approach/2422870 The asymmetric syntheses of (−)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin are described herein. The ring-closing iodoamination of two epimeric bishomoallylic amines to give the corresponding 5-iodomethylpyrrolidines was followed by in situ ring-expansion to give two diastereoisomerically pure (>99:1 dr) cyclic carbonates. Subsequent deprotection gave (−)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin as single diastereoisomers in 7.4 and 3.3% overall yield, respectively, from commercially available starting materials.