SYNTHESIS AND INVESTIGATION OF A HINDERED, CHIRAL, BICYCLIC GUANIDINE

Authors
DAVIS AP DEMPSEY KJ
Citation
Ap. Davis et Kj. Dempsey, SYNTHESIS AND INVESTIGATION OF A HINDERED, CHIRAL, BICYCLIC GUANIDINE, Tetrahedron : asymmetry, 6(11), 1995, pp. 2829-2840
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
11
Year of publication
1995
Pages
2829 - 2840
Database
ISI
SICI code
0957-4166(1995)6:11<2829:SAIOAH>2.0.ZU;2-7
Abstract
Chiral amidines and guanidines have potential as enantioselective cata lysts for reactions of nitroalkanes, through formation of hydrogen-bon ded complexes with nitronate anions. With this in mind, the bicyclic g uanidine 9 was synthesized from amino-alcohol 12, employing pyrrole fo rmation as a protection method for the amino-nitrogen. Low enantiosele ctivities were obtained when 9 was used as catalyst for conjugate addi tions of nitroalkanes. However, other applications are suggested by it s hindered, chiral and strongly basic nature.