Vinylogous Mannich reactions: some theoretical studies on the origins of diastereoselectivity.
[reaction: see text] Ab initio calculations at the RHF/3-21G level were used to investigate the limiting transition states in the addition of 2-methoxyfuran to a pyrrolinium ion. Four stationary points were found on the potential energy surface with relative energies of threo Diels-Alder, 0.0 kcal/mol; erythro open, 0.9 kcal/mol; erythro Diels-Alder, 1.3 kcal/mol; and threo open, 1.8 kcal/mol.
Bur
S K
SK
Department of Chemistry and Biochemistry, The University of Texas, Austin, Texas 78712, USA. sbur@emory.edu
Martin
S F
SF
D002151:Calorimetry; D005663:Furans; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014753:Vinyl Compounds / Q000737:chemistry*
D005663:Furans; D011758:Pyrroles; D014753:Vinyl Compounds