N-AMINOAZIRIDINYLHYDRAZONES - HIGHLY DIASTEREOSELECTIVE ALKYLATION WITHOUT CHELATION, AND A SYN-DIRECTING EFFECT

Authors
AUGERI DJ CHAMBERLIN AR
Citation
Dj. Augeri et Ar. Chamberlin, N-AMINOAZIRIDINYLHYDRAZONES - HIGHLY DIASTEREOSELECTIVE ALKYLATION WITHOUT CHELATION, AND A SYN-DIRECTING EFFECT, Tetrahedron letters, 35(31), 1994, pp. 5599-5602
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
31
Year of publication
1994
Pages
5599 - 5602
Database
ISI
SICI code
0040-4039(1994)35:31<5599:N-HDAW>2.0.ZU;2-I
Abstract
The alkylation of C-2-symmetric N-aminoaziridinylhydrazone anions show s excellent diastereoselectivity despite the absence of chelating grou ps in the chiral auxiliary. In contrast to other dialkylhydrazones, az iridinylhydrazones exhibit a syn-directing effect analogous to that ob served for arenesulfonylhydrazones.