Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr3-initiated three component, one-pot cascade

  • Hinkle R
  • Lian Y
  • Speight L
 et al. 
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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). © 2009 Elsevier Ltd. All rights reserved.

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Authors

  • Robert J. Hinkle

  • Yajing Lian

  • Lee C. Speight

  • Heather E. Stevenson

  • Melissa M. Sprachman

  • Lauren A. Katkish

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