Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines

Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines Full article

Journal

Tetrahedron
ISSN: 0040-4020 , E-ISSN: 1464-5416

Output data

Year: 2009, Volume: 65, Number: 23, Pages: 4578-4592 Pages count : 15 DOI: 10.1016/j.tet.2009.03.082

Authors

Tabolin Andrey A. ¹ , Lesiv Alexey V. ¹ , Khomutova Yulia A. ¹ , Nelyubina Yulia V. ² , Ioffe Sema L. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 47, Moscow 119991, Russian Federation
2	A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, Moscow 119991, Russian Federation

A new approach toward the synthesis of 3-α-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.

Tabolin A.A. , Lesiv A.V. , Khomutova Y.A. , Nelyubina Y.V. , Ioffe S.L.
Rearrangement of 3-alkylidene-2-siloxy-tetrahydro-1,2-oxazines (ASENA). A new approach toward the synthesis of 3-α-hydroxyalkyl-5,6-dihydro-4H-1,2-oxazines
Tetrahedron. 2009. V.65. N23. P.4578-4592. DOI: 10.1016/j.tet.2009.03.082 WOS Scopus OpenAlex

≡ Web of science:	WOS:000266431600016
≡ Scopus:	2-s2.0-65449142781
≡ OpenAlex:	W2952565814