Oxazaborolidinone-catalyzed enantioselective Friedel-Crafts alkylation of furans and indoles with alpha,beta-unsaturated ketones.
allo-Threonine-derived oxazaborolidinone (10 mol %) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic alpha,beta-unsaturated ketones to give products with high yield and high enantioselectivity. The use of N,N-dimethylaniline (2.5-10 mol %) as an additive is essential for enantioselectivity.
Adachi
Shinya
S
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, Japan 606-8585.
Tanaka
Fumi
F
Watanabe
Kazuya
K
Harada
Toshiro
T
D000478:Alkylation; D001880:Boranes / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006573:Heterocyclic Compounds, 1-Ring / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D001880:Boranes; D005663:Furans; D006573:Heterocyclic Compounds, 1-Ring; D007211:Indoles; D007659:Ketones; C527334:oxazaborolidinone