Stereoselective epoxidation of 4-deoxypentenosides: a polarized-pi model.
The high facioselectivity in the epoxidation of 4-deoxypentenosides (4-DPs) by dimethyldioxirane (DMDO) correlates with a stereoelectronic bias in the 4-DPs' ground-state conformations, as elucidated by polarized-pi frontier molecular orbital (PPFMO) analysis.
Cheng
Gang
G
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, USA.
Boulineau
Fabien P
FP
Liew
Siong-Tern
ST
Shi
Qicun
Q
Wenthold
Paul G
PG
Wei
Alexander
A
D000475:Alkenes / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D008958:Models, Molecular
D000475:Alkenes; D004852:Epoxy Compounds