Asymmetric synthesis of alpha-amino 1,3-dithioketals from sulfinimines (N-sulfinyl imines). Synthesis of (2S,3R)-(-)-3-hydroxy-3-methylproline.
[reaction: see text] N-Sulfinyl alpha-amino 1,3-dithioketals are prepared in high de and good yield by treating sulfinimines with lithio-1,3-dithianes. Selective removal of the N-sulfinyl or the thioketal groups affords stable alpha-amino 1,3-dithioketals and N-sulfinyl alpha-amino ketones, respectively. This new sulfinimine-derived chiral building block is employed in the asymmetric synthesis of polyoxypeptin amino acid (2S,3R)-(-)-3-hydroxy-3-methylproline.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Ramachandar
Tokala
T
Liu
Hu
H
D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D011392:Proline / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000032:analysis / Q000737:chemistry*
C449928:(2,3)-3-hydroxy-3-methylproline; D007202:Indicators and Reagents; D013457:Sulfur Compounds; D011392:Proline