Direct alpha-oxytosylation of carbonyl compounds: one-pot synthesis of heterocycles.
N-Methyl-O-tosylhydroxylamine is an effective reagent for the direct alpha-oxytosylation of carbonyl compounds. The reactions proceed smoothly at room temperature in the presence of both moisture and air and functional group tolerance in the substrate is good. With nonsymmetrical substrates regioselectivity for primary over secondary centers is observed and complete regiospecificity for primary over tertiary centers is obtained. Addition of a bis-heteronucleophile directly to the crude reaction mixture in a one-pot process leads to the corresponding heterocyclic product.
John
Oliver R S
OR
School of Chemistry, Main Building, Cardiff University, Park Place, Cardiff, CF10 3AT, United Kingdom.
Killeen
Niall M
NM
Knowles
Deborah A
DA
Yau
Sze Chak
SC
Bagley
Mark C
MC
Tomkinson
Nicholas C O
NC