Journal of the American Chemical Society
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In conclusion, we have demonstrated the chemoselective
generation of carbanions in the presence of dialkyl peroxides
and the application of the resulting intermediates to establish
new C−O bonds. This alternative to more traditional
etherifications provides a new approach to synthesis of
spirocyclic ethers, aryl ethers, and various oxacycles including
oxetanes.
ASSOCIATED CONTENT
■
S
* Supporting Information
1
Experimental procedures, spectral listings, and selected H and
13C NMR data. This material is available free of charge via the
AUTHOR INFORMATION
Corresponding Author
■
Present Address
†Teva Pharmaceuticals, Salt Lake City, UT.
Author Contributions
‡These authors contributed equally.
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
■
The authors wish to acknowledge Navid Rahmany for his
contributions to synthesis of a cyclization precursor. Research
was conducted with funding from the NSF (CHE 1057982) in
facilities renovated with funding from NIH (RR016544).
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