Back to Search
Start Over
Organocatalytic Enantioselective Acyloin Rearrangement of α-Hydroxy Acetals to α-Alkoxy Ketones.
- Source :
- Angewandte Chemie; 5/15/2017, Vol. 129 Issue 21, p5952-5955, 4p
- Publication Year :
- 2017
-
Abstract
- We report an unprecedented organocatalytic enantioselective acyloin rearrangement of α,α-disubstituted α-hydroxy acetals. In the presence of a catalytic amount of chiral binol-derived N-triflyl phosphoramide, α-hydroxy acetals rearranged to α-alkoxy ketones in good to high yields with high enantioselectivities. Formation of an ion pair between the in situ generated oxocarbenium ion and the chiral phosphoramide anion was proposed to be responsible for the highly efficient transfer of chirality. Conditions for removal of cyclohexyl and cyclopentyl groups from the corresponding α-alkoxy ketones were uncovered underpinning their potential general utility as hydroxy protecting groups. Conversion of the rearranged products to the enantioenriched α-hydroxy ketone, 1,2-diol, β-amino alcohol and 1,4-dioxane was also documented. [ABSTRACT FROM AUTHOR]
- Subjects :
- ORGANOCATALYSIS
ENANTIOSELECTIVE catalysis
KETONES
CHIRALITY
CHEMICAL reactions
Subjects
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 129
- Issue :
- 21
- Database :
- Complementary Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 122918633
- Full Text :
- https://doi.org/10.1002/ange.201701098