Journal article
Diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus
- Abstract:
-
The diastereoselective [2,3]-sigmatropic rearrangements of lithium N-benzyl-O-allylhydroxylamides bearing a stereogenic centre adjacent to the migration terminus are examined. (E)-N-Benzyl-O-(4-phenylpent-2-enyl)-hydroxylamine rearranges in 30% de to afford syn-(3RS,4RS)-3-(N-benzyl-N-hydroxy)-4-phenylpent-1-ene as the major diastereoisomer, consistent with the rearrangement proceeding under moderate steric control. Rearrangements of both lithium (E)- and (Z)-N-benzyl-O-(4-methoxy-4-phenylbut...
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- Publication status:
- Published
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- Publisher copy:
- 10.1039/b207069n
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Bibliographic Details
- Journal:
- JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
- Issue:
- 19
- Pages:
- 2141-2150
- Publication date:
- 2002-01-01
- DOI:
- EISSN:
-
1364-5463
- ISSN:
-
1472-7781
- URN:
-
uuid:a4e637d2-7338-43fe-99f3-1eb45e8ea91b
- Source identifiers:
-
38431
- Local pid:
- pubs:38431
Item Description
- Language:
- English
Terms of use
- Copyright date:
- 2002
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