- Abstract:
- 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.
- Publication status:
- Published
- Publisher copy:
- 10.1021/ol400735z
-
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- Journal:
- Organic letters
- Volume:
- 15
- Issue:
- 8
- Pages:
- 2042-2045
- Publication date:
- 2013-04-05
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- URN:
-
uuid:8f73d27b-7090-40ac-bd02-d0a438398aac
- Source identifiers:
-
394908
- Local pid:
- pubs:394908
- Language:
- English
- Keywords:
- Copyright date:
- 2013
Journal article
Asymmetric syntheses of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin via a ring-expansion approach.
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