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Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr3-initiated three component, one-pot cascade
Hinkle, Robert J. Lian, Yajing Speight, Lee C. Stevenson, Heather E. Sprachman, Melissa M. Katkish, Lauren A. Mattern, M. Christa
Hinkle, Robert J.
Lian, Yajing
Speight, Lee C.
Stevenson, Heather E.
Sprachman, Melissa M.
Katkish, Lauren A.
Mattern, M. Christa
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 beta,gamma-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). (C) 2009 Elsevier Ltd. All rights reserved.
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2009-01-01
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synthesis_2_6.pdf
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Chemistry
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10.1016/j.tet.2009.06.083