CONJUGATE ADDITION OF AMINES AND THIOLS TO (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - PREPARATION OF ENANTIOPURE N-ACYLIMINIUM ION PRECURSORS

Authors
KOOT WJ HIEMSTRA H SPECKAMP WN
Citation
Wj. Koot et al., CONJUGATE ADDITION OF AMINES AND THIOLS TO (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - PREPARATION OF ENANTIOPURE N-ACYLIMINIUM ION PRECURSORS, Tetrahedron : asymmetry, 4(8), 1993, pp. 1941-1948
Citations number
36
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
4
Issue
8
Year of publication
1993
Pages
1941 - 1948
Database
ISI
SICI code
0957-4166(1993)4:8<1941:CAOAAT>2.0.ZU;2-4
Abstract
Conjugate addition reactions of amines and thiols to enantiopure (R)-1 -acetyl-5-isopropoxy-3-pyrrolin-2-one are shown to proceed with high s tereoselectivity. The benzylamine and the benzyl mercaptan adducts wer e N-deacylated and then treated with Lewis acid to effect N-acyliminiu m cyclization. This cyclization proceeded smoothly with the benzyl mer captan adduct. The benzylamine adduct only cyclized after amine protec tion with the Boc group, but then led to an enantiopure oxazolidinone.