- Abstract:
-
Oxidation of enantiomerically pure (R)-N(1)-1'-(1''-naphthyl)ethyl-2,7-dihydro-1H-azepine with m-CPBA in the presence of HBF(4) and BnOH gave (3S,4R,5S,6S,1'R)-N(1)-1'-(1''-naphthyl)ethyl-3-hydroxy-4-benzyloxy-5,6-epoxyazepane as the major product and as a single diastereoisomer after chromatography. Elaboration of this highly functionalized intermediate via ring contraction to (2S,3R,4S,5S,1'R)-N(1)-benzyl-2-chloromethyl-3-benzyloxy-4,5-epoxypiperidine followed by regioselective epoxide ring...
Expand abstract - Publication status:
- Published
- Publisher copy:
- 10.1021/jo101756g
-
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- Journal:
- The Journal of organic chemistry
- Volume:
- 75
- Issue:
- 23
- Pages:
- 8133-8146
- Publication date:
- 2010-12-05
- DOI:
- EISSN:
-
1520-6904
- ISSN:
-
0022-3263
- URN:
-
uuid:a2c70645-c26b-49c7-9f0b-bd1df393f3fe
- Source identifiers:
-
110642
- Local pid:
- pubs:110642
- Language:
- English
- Keywords:
- Copyright date:
- 2010
Journal article
Syntheses of the enantiomers of 1-deoxynojirimycin and 1-deoxyaltronojirimycin via chemo- and diastereoselective olefinic oxidation of unsaturated amines.
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