BORANES IN SYNTHESIS .2. ASYMMETRIC-SYNTHESIS OF BETA-AMINO ALCOHOLS - A FACILE CONVERSION OF ALPHA-AMINO ACETOPHENONES TO THE CORRESPONDING BETA-AMINO ALCOHOLS IN HIGH ENANTIOMERIC PURITY

Authors
BEARDSLEY DA FISHER GB GORALSKI CT NICHOLSON LW SINGARAM B
Citation
Da. Beardsley et al., BORANES IN SYNTHESIS .2. ASYMMETRIC-SYNTHESIS OF BETA-AMINO ALCOHOLS - A FACILE CONVERSION OF ALPHA-AMINO ACETOPHENONES TO THE CORRESPONDING BETA-AMINO ALCOHOLS IN HIGH ENANTIOMERIC PURITY, Tetrahedron letters, 35(10), 1994, pp. 1511-1514
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
10
Year of publication
1994
Pages
1511 - 1514
Database
ISI
SICI code
0040-4039(1994)35:10<1511:BIS.AO>2.0.ZU;2-3
Abstract
The asymmetric reduction of 2-amino acetophenones with Ipc(2)BH or Ipc (2)BCl at -78 degrees C, yields the corresponding beta-amino alcohols in good to excellent yields. Although only modest (12-45% ee) enantiom eric excesses were obtained with Ipc(2)BH, 75-99% enantiomeric excesse s were obtained when Ipc(2)BCl was used as the asymmetric reducing age nt.