期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 76, 期 22, 页码 9269-9277出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo201478d
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资金
- National Institutes of Health [RGM072525-01A2]
- Camille and Henry Dreyfus Foundation
- Beckman Scholars' Program
- Roy R. Charles Center of the College of William Mary
- Howard Hughes Medical Institute
- NSF [CHE-0443345]
- College of William Mary
Catalytic quantities of bismuth(III) triflate efficiently initiate the rearrangement of epoxides to aldehydes, which subsequently react with (Z)-delta-hydroxyalkenylsilanes to afford 2,6-disubstituted 3,6-dihydro-2H-pyrans. Isolated yields of desired products using Bi(OTf)(3) were compared with yields obtained when the reactions were run with TfOH and TMSOTf in the presence and absence of several additives. These studies, as well as NMR spectroscopic analyses, indicate an initial Lewis acid/base interaction between Bi(OTf)(3) and substrates providing TfOH in situ.
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