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Communication | Special issue | Vol 84, No. 1, 2012, pp.385-391
Published online, 31st August, 2011
DOI: 10.3987/COM-11-S(P)85
Enantioenriched Formation of Synthons of 1,5-Hexadiene Bis-epoxides for Construction of Nonracemic cis- and trans-2,5-Disubstituted Tetrahydrofurans

David R. Williams* and Ramkrishna De

*Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, IN 47405-7102, U.S.A.


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.