5 years ago

β-Silyl-Assisted Tandem Diels–Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones

β-Silyl-Assisted Tandem Diels–Alder/Nazarov Reaction of 1-Aryl-3-(trimethylsilyl) Ynones
Wesley A. Chalifoux, Punyanuch Sophanpanichkul, Rachael A. Carmichael
A one-pot tandem Diels–Alder/Nazarov reaction of 1-aryl-3-(trimethylsilyl) ynones has been achieved to generate carbo- and heterocyclic fused ring systems in good to excellent yields. The β-silyl effect is instrumental in accessing this otherwise challenging cascade annulation reaction. The tandem reaction proceeds in the presence of BCl3 to generate three new carbon–carbon bonds, a quaternary carbon, and two stereogenic centers with excellent diastereocontrol. A variety of substituted arenes, and even heteroaromatics, are tolerated to provide tricyclic products that are of interest as advanced intermediates toward biologically relevant compounds.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00911

DOI: 10.1021/acs.orglett.7b00911

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