期刊
TETRAHEDRON
卷 65, 期 34, 页码 6834-6839出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.06.083
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资金
- National Institutes of Health [RGM072525-01A2]
- Tomas F. and Kate Miller Jeffress Memorial Trust
- Camille and Henry Dreyfus Foundation
- GlaxoSmithKline
- Pfizer Pharmaceuticals
- The Beckman Scholars' Program
- Eli Lilly Undergraduate Fellowship Program
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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