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Synthesis 2005(15): 2549-2561
DOI: 10.1055/s-2005-872122
DOI: 10.1055/s-2005-872122
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Single-Enantiomer 6-Hydroxy-7-phenyl-1,4-oxazepan-5-ones
Weitere Informationen
Received
18 January 2005
Publikationsdatum:
04. August 2005 (online)
Publikationsverlauf
Publikationsdatum:
04. August 2005 (online)
![](https://www.thieme-connect.de/media/synthesis/200515/lookinside/thumbnails/10.1055-s-2005-872122-1.jpg)
Abstract
An efficient two-step preparation of (6R,7R)-6-hydroxy-7-phenyl-1,4-oxazepan-5-ones (1) starting from aminoethanols and (2R,3S)-3-phenyloxirane-2-carboxylic ethyl ester or potassium salt has been described. The most efficient catalyst identified for the ring closure of the resulting intermediate epoxyamides was Sc(OTf)3. By choice of appropriate chiral starting substituted aminoethanol and 3-phenyloxirane-2-carboxylic derivatives, the procedure allows facile synthesis of other single enantiomer 6-hydroxy-7-phenyl-1,4-oxazepan-5-ones.
Key words
heterocycles - ring closure - epoxides - scandium - magnesium
- 1
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References
Manuscript in progress.