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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Bibliographic Details
Published inTetrahedron Vol. 65; no. 23; pp. 4578 - 4592
Main Authors Tabolin, Andrey A., Lesiv, Alexey V., Khomutova, Yulia A., Nelyubina, Yulia V., Ioffe, Sema L.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 06.06.2009
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Prolinoles
Silylation
1,2-Oxazine-N-oxides
6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES
STEREOSELECTIVE-SYNTHESIS
1,2-Oxazines
DERIVATIVES
NITROALKENE
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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.
ISSN:0040-4020
DOI:10.1016/j.tet.2009.03.082