Ontology highlight
ABSTRACT:
SUBMITTER: Zhang Z
PROVIDER: S-EPMC7050190 | biostudies-literature | 2019 Sep
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20190815 17
[2,3]-Sigmatropic rearrangements (Wittig rearrangements) of α-alkoxy oxazolidinone enolates are described. Whereas alkali metal enolates fail, owing to facile deacylation, boron enolates generated from di-<i>n</i>-butylboron triflate and triethylamine rearranged in good yields and high selectivities with exceptions noted. IR and NMR spectroscopies show the boron is chelated by the α-alkoxy group rather than the more distal oxazolidinone carbonyl in the complex and enolate. The rearrangement prod ...[more]