SIMPLE SYNTHESIS OF 2H-1,3-OXAZINES AND THEIR STEREOSELECTIVE TRANSFORMATION INTO 1,3-AMINOALCOHOLS AND AZETIDINES

Authors
BARLUENGA J TOMAS M BALLESTEROS A KONG JS
Citation
J. Barluenga et al., SIMPLE SYNTHESIS OF 2H-1,3-OXAZINES AND THEIR STEREOSELECTIVE TRANSFORMATION INTO 1,3-AMINOALCOHOLS AND AZETIDINES, Tetrahedron, 52(9), 1996, pp. 3095-3106
Citations number
44
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
9
Year of publication
1996
Pages
3095 - 3106
Database
ISI
SICI code
0040-4020(1996)52:9<3095:SSO2AT>2.0.ZU;2-F
Abstract
4-Amino-1-azadienes 1 undergo cyclization at 20-50 degrees C with este rs of glyoxylic acid giving rise to 2H-1.3-oxazines 3. These compounds are reduced with NaBH3CN / AcOH affording stereoselectively syn, syn- 1.3-aminoalcohols 4, which are further O-mesylated and cyclized to yie ld azetidines 7 with a cis, trans stereochemistry.