STEREOSELECTIVE REACTION OF A CHIRAL ASSISTED AMIDE ENOLATE ION WITH 1-IODONAPHTHALENE BY THE S(RN)1 MECHANISM

Authors
LOTZ GA PALACIOS SM ROSSI RA
Citation
Ga. Lotz et al., STEREOSELECTIVE REACTION OF A CHIRAL ASSISTED AMIDE ENOLATE ION WITH 1-IODONAPHTHALENE BY THE S(RN)1 MECHANISM, Tetrahedron letters, 35(42), 1994, pp. 7711-7714
Citations number
10
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
42
Year of publication
1994
Pages
7711 - 7714
Database
ISI
SICI code
0040-4039(1994)35:42<7711:SROACA>2.0.ZU;2-F
Abstract
The photostimulated reaction of the chiral assisted amide enolate ion 1 with 1-iodonaphtalene 2 gave the isomeric substitution products 3 wi th diastereomeric excess depending of the counter ion. Li+ (at -78 deg rees C) and Ti(IV) were found to be the most effective (the diastereom eric ratio > 99). These reactions were done in liquid ammonia and are suspected to follow the S(RN)1 mechanism.