CNS AGENTS - OPTICAL RESOLUTION WITH BAKERS-YEAST AS KEY STEP IN THE SYNTHESIS OF OPTICALLY-ACTIVE TRICYCLIC AMINES

Authors
WUNSCH B DIEKMANN H
Citation
B. Wunsch et H. Diekmann, CNS AGENTS - OPTICAL RESOLUTION WITH BAKERS-YEAST AS KEY STEP IN THE SYNTHESIS OF OPTICALLY-ACTIVE TRICYCLIC AMINES, Heterocycles, 38(4), 1994, pp. 709-712
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
38
Issue
4
Year of publication
1994
Pages
709 - 712
Database
ISI
SICI code
0385-5414(1994)38:4<709:CA-ORW>2.0.ZU;2-I
Abstract
The synthesis of the optically active 4,5,6-tetrahydro-N-methyl-1H-2-b enzoxocin-6-amines ((-)-10) and ((+)-10) is achieved by optical resolu tion of the racemic 1,5-epoxy-4,5-dihydro-1H-2-benzoxocin-6(3H)-one (( +)-8) with baker's yeast as the key step. (+)-10 can also be prepared starting with the homochiral alpha-hydroxy-gamma-butyroloctone ((-)-6a ), which is easily obtained from (S)-(-)-malic acid.