Journal
SYNTHESIS-STUTTGART
Volume 51, Issue 7, Pages 1561-1564Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1610356
Keywords
strained molecules; allenes; alkynes; enolate; isomerization; lithiation; rearrangement; solvent effects
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Funding
- JSPS KAKENHI [JP16K05774, JP16H01153, JP18H04413]
- Kawanishi Memorial ShinMaywa Education Foundation
- Japan Science Society
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This study investigated a practical method for regiocontrolled synthesis of precursors of strained cyclohexynes and 1,2-cyclohexadienes, which is a one-pot procedure consisting of a rearrangement of silyl enol ether and subsequent formation of the enol triflates. Triethylsilyl enol ether, derived from cyclohexanone, was treated with a combination of LDA and-BuOK in-hexane/THF to encourage the migration of the silyl group to generate an -silyl enolate. Subsequently, the -silyl enolate was reacted with Comins' reagent to yield the corresponding enol triflate. Finally, the -silylated trisubstituted lithium enolate for the synthesis of 1,2-cyclohexadiene precursor was isomerized in the presence of a stoichiometric amount of water for one hour at room temperature to exclusively provide tetrasubstituted lithium enolate for the synthesis of cyclohexyne precursor in one pot.
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