Enantioselective synthesis of 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans via [4 + 2] cycloaddition and ring-opening cross-metathesis |
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Authors: | Benjamin Noah M Martin Stephen F |
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Institution: | Department of Chemistry & Biochemistry, The University of Texas at Austin, Austin, Texas 78712, USA. |
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Abstract: | A chiral vinyl sulfoxide has been developed that undergoes highly diastereoselective Diels-Alder cycloadditions with various substituted furans in excellent yield. The cycloadducts can be stereoselectively transformed into 2,2,5-tri- and 2,2,5,5-tetrasubstituted tetrahydrofurans, which are structural subunits of many natural products, via regioselective ring-opening metathesis/cross-metathesis or oxidative cleavage/refunctionalization. |
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