Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr3-initiated three component, one-pot cascade |
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Authors: | Robert J Hinkle Yajing Lian Lee C Speight Heather E Stevenson Melissa M Sprachman Lauren A Katkish M Christa Mattern |
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Institution: | Department of Chemistry, The College of William & Mary, PO Box 8795, Williamsburg, VA 23187-8795, USA |
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Abstract: | The rapid synthesis of cis-2,6-disubstituted dihydropyrans is achieved in a three-component, one-pot cascade reaction. BiBr3-mediated addition of ketene silyl acetals or silyl enol ethers to β,γ-unsaturated cis-4-trimethylsilyl-3-butenal provides a Mukaiyama aldol adduct containing a vinylsilane moiety tethered to a silyl ether. Addition of a second aldehyde initiates a domino sequence involving intermolecular addition followed by an intramolecular silyl-modified Sakurai (ISMS) reaction. Isolated yields of this one-pot reaction vary from 44 to 80% and all compounds were isolated as the cis-diastereomers (10 examples). |
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