STEREOCHEMISTRY OF DIELS-ALDER REACTION AT HIGH-PRESSURE:INFLUENCE OF PRESSURE ON ASYMMETRIC INDUCTION IN (4+2)CYCLOADDITION OF 1-METHOXYBUTA-1,3-DIENE TO 2,3-O-ISOPROPYLIDENE-D-GLYCERALDEHYDE

Article abstract of DOI:10.1016/S0040-4020(01)88056-X

High pressure (4+2)cycloaddition of 1-methoxybuta-1,3-diene (1) to 2,3-O-isopropylidene-D-glyceraldehyde (2) afforded four diastereoisomeric 6-substituted 2-methoxy-5,6-dihydro-2H-pyrans (3), for which the diastereoisomeric excess and absolute configuration were determined.The effects of pressure, temperature and solvent on asymmetric induction were examined.Stereochemical models were used for interpretation of the results.