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- Title
Organocatalytic Enantioselective Vinylogous Pinacol Rearrangement Enabled by Chiral Ion Pairing.
- Authors
Wu, Hua; Wang, Qian; Zhu, Jieping
- Abstract
An enantioselective pinacol rearrangement of functionalized ( E)-2-butene-1,4-diols was developed. In the presence of a catalytic amount of a chiral BINOL-derived N-triflyl phosphoramide, these 1,4-diols rearranged to β,γ-unsaturated ketones in excellent yields and enantioselectivities. The formation of a chiral ion pair between the intermediary allylic cation and the chiral phosphoramide anion was postulated to be responsible for the highly efficient chirality transfer. These chiral building blocks were further converted into enantioenriched polysubstituted tetrahydrofuran and tetrahydronaphthalene derivatives.
- Subjects
ORGANOCATALYSIS; ENANTIOSELECTIVE catalysis; PINACOL rearrangement; PHOSPHORAMIDES; KETONES; TETRAHYDROFURAN
- Publication
Angewandte Chemie, 2016, Vol 128, Issue 49, p15637
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201609911