Document Type
Article
Department/Program
Chemistry
Journal Title
Tetrahedron
Pub Date
2009
Volume
65
Issue
34
First Page
6834
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.
Recommended Citation
Hinkle, Robert J.; Lian, Yajing; Speight, Lee C.; Stevenson, Heather E.; Sprachman, Melissa M.; Katkish, Lauren A.; and Mattern, M. Christa, Synthesis of 2,6-disubstituted dihydropyrans via an efficient BiBr3-initiated three component, one-pot cascade (2009). Tetrahedron, 65(34), 6834-6839.
10.1016/j.tet.2009.06.083
DOI
10.1016/j.tet.2009.06.083
