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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.

Original publication

DOI

10.1021/ol400735z

Type

Journal article

Journal

Org Lett

Publication Date

19/04/2013

Volume

15

Pages

2042 - 2045

Keywords

1-Deoxynojirimycin, Amines, Carbonates, Catalysis, Crystallography, X-Ray, Molecular Conformation, Molecular Structure, Stereoisomerism