ENANTIOENRICHED FORMATION OF SYNTHONS OF 1,5-HEXADIENE BIS-EPOXIDES FOR CONSTRUCTION OF NONRACEMIC CIS- AND TRANS-2,5-DISUBSTITUTED TETRAHYDROFURANS

摘要

A pathway for the synthesis of enantioenriched bis-epoxides derived from 2,6-heptadien-1-ol is described. Use of the Katsuki titanium salalen catalyst affords high asymmetric induction for mild epoxidation of the monosubstituted alkene as the key step. Regioselective nucleophilic additions to these chiral bis-epoxides lead to a stereocontrolled preparation of nonracemic cis-and trans-2,5-disubstituted tetrahydrofurans.