ASYMMETRIC ADDITION-REACTION OF ORGANOZINC REAGENTS TO NITRONES USINGA CATALYTIC AMOUNT OF EXTERNAL CHIRAL AUXILIARY

Authors
UKAJI Y KENMOKU Y INOMATA K
Citation
Y. Ukaji et al., ASYMMETRIC ADDITION-REACTION OF ORGANOZINC REAGENTS TO NITRONES USINGA CATALYTIC AMOUNT OF EXTERNAL CHIRAL AUXILIARY, Tetrahedron : asymmetry, 7(1), 1996, pp. 53-56
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
1
Year of publication
1996
Pages
53 - 56
Database
ISI
SICI code
0957-4166(1996)7:1<53:AAOORT>2.0.ZU;2-V
Abstract
Catalytic asymmetric addition reactions of dialkylzinc to nitrones are realized; i.e., in the presence of a catalytic amount of bromomagnesi um -4-dimethylamino-1,2-diphenyl-3-methyl-2-butoxide, dialkylzincs wer e reacted with 3,4-dihydroisoquinoline N-oxide derivatives to give the corresponding 1-alkylated hydroxylamines enantioselectively. In order to achieve higher stereoselection, addition of bromomagnesium triphen ylmethoxide was crucial.