INTRAMOLECULAR AMIDOALKYLATION OF CHIRAL IMINES AND IMINIUM IONS - STEREOSELECTIVE SYNTHESIS OF ANTI-1,2-AMINOALCOHOL AND ANTI-1,3-AMINOALCOHOL

Authors
HIOKI H IZAWA T YOSHIZUKA M KUNITAKE R ITO S
Citation
H. Hioki et al., INTRAMOLECULAR AMIDOALKYLATION OF CHIRAL IMINES AND IMINIUM IONS - STEREOSELECTIVE SYNTHESIS OF ANTI-1,2-AMINOALCOHOL AND ANTI-1,3-AMINOALCOHOL, Tetrahedron letters, 36(13), 1995, pp. 2289-2292
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
13
Year of publication
1995
Pages
2289 - 2292
Database
ISI
SICI code
0040-4039(1995)36:13<2289:IAOCIA>2.0.ZU;2-E
Abstract
When treated with Lewis acids, 2- or 3-vinyl- or -phenylsiloxyaminoace tals generated the corresponding imines or iminium ions which in turn underwent smooth intramolecular amidoalkylation to afford anti-1,2- or -1,3-aminoalcohol derivatives in very high chemical yields and excell ent diastereomeric ratios. Applying the reaction, Z-allo-L-threonine a nd (+/-)-N-ethoxycarbonyl-anti-gamma-hydroxynorvaline were successfull y synthesized.