Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-alpha-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines
A new approach toward the synthesis of 3-alpha-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines 1 from available 5,6-dihydro-4H-1,2-oxazine N-oxides 2 has been described. The key step of the process-the rearrangement of 3-alkiliden-2-siloxy-tetrahydro-1,2-oxazines 3 (ASENA)-was thoroughly investigated. Opti...
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Published in | Tetrahedron Vol. 65; no. 23; pp. 4578 - 4592 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
OXFORD
Elsevier
06.06.2009
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Subjects | |
Online Access | Get full text |
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Summary: | A new approach toward the synthesis of 3-alpha-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines 1 from available 5,6-dihydro-4H-1,2-oxazine N-oxides 2 has been described. The key step of the process-the rearrangement of 3-alkiliden-2-siloxy-tetrahydro-1,2-oxazines 3 (ASENA)-was thoroughly investigated. Optimal experimental conditions were developed. A possible pathway of the ASENA rearrangement was proposed. (C) 2009 Elsevier Ltd. All rights reserved. |
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ISSN: | 0040-4020 |
DOI: | 10.1016/j.tet.2009.03.082 |