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

被引：28

作者：

Tabolin, Andrey A. ^{[1
]}

Lesiv, Alexey V. ^{[1
]}

Khomutova, Yulia A. ^{[1
]}

Nelyubina, Yulia V. ^{[2
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinskii Organ Chem Inst, Moscow 119991, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organomet Cpds Inst, Moscow 119991, Russia

来源：

TETRAHEDRON | 2009年 / 65卷 / 23期

关键词：

1,2-Oxazines; 1,2-Oxazine-N-oxides; Silylation; Prolinoles; 6-SILOXY-SUBSTITUTED 5,6-DIHYDRO-4H-1,2-OXAZINES; STEREOSELECTIVE-SYNTHESIS; DERIVATIVES; NITROALKENE;

D O I：

10.1016/j.tet.2009.03.082

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4578 / 4592

页数：15

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