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.