6533b7d3fe1ef96bd12608d9
RESEARCH PRODUCT
Regio- and stereoselective synthesis of constrained enantiomeric β-amino acid derivatives
Tamás A. MartinekZsolt SzakonyiFerenc FülöpReijo Sillanpääsubject
chemistry.chemical_classificationChlorosulfonyl isocyanateStereochemistryOrganic ChemistryCatalysisAmino acidInorganic Chemistrychemistry.chemical_compoundStereospecificitychemistryAb initio quantum chemistry methodsStereoselectivityPhysical and Theoretical ChemistryEnantiomerIsomerizationdescription
Abstract Chlorosulfonyl isocyanate addition to (−)- and (+)-apopinene furnished monoterpene-fused β-lactams in highly regio- and stereospecific reactions. β-Lactams 5 and 13 exhibited reactivities similar to those of the cycloalkane-fused analogs and were easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis -amino ester afforded the corresponding trans -amino acid enantiomers in excellent yields. The complete isomerization is explained by the stability difference, which was estimated by ab initio calculations between the cis- and trans -diastereomers.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2008-10-01 | Tetrahedron: Asymmetry |