Enantioselective direct intermolecular aldol reactions with enantiotopic group selectivity and dynamic kinetic resolution.
[reaction: see text] Proline-catalyzed aldol reactions of tetrahydro-4H-thipyranone with racemic 1,4-dioxa-8-thia-spiro[4.5]decane-6-carboxaldehyde and with meso/dl 1,4-dioxa-8-thiaspiro[4.5]decane-6,10-dicarboxaldehyde proceed with dynamic kinetic resolution and give single adducts in good yields with excellent ee's. The high enantiotopic group selectivity results from the high intrinsic diastereoface selectivity of the aldehydes. These reactions significantly extend the scope of the enantioselective direct aldol reaction and constitute simple and efficient syntheses of useful tetrapropionate synthons.
Ward
Dale E
DE
Department of Chemistry, University of Saskatchewan, Saskatoon SK S7N 5C9, Canada. dale.ward@usask.ca
Jheengut
Vishal
V
Akinnusi
Olukayode T
OT