Lewis acid-catalyzed one-pot sequential reaction for the synthesis of α-halogenated β-keto esters

Tetrahedron Letters

Volumn 51, Issue 17, 2010, Pages 2374-2377

  Cui, Han Feng ^a   Dong, Ke Yan ^a   Nie, Jing ^a   Zheng, Yan ^a   Ma, Jun An ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

Ketoester; Halogenation; Lewis acid; One pot reaction

Indexed keywords

ALDEHYDE; ESTER; HALIDE; KETONE; LEWIS ACID;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; ELECTRON TRANSPORT; HALOGENATION; KNOEVENAGEL CONDENSATION; ONE POT SYNTHESIS; STEREOCHEMISTRY;

EID: 77949571002     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.02.158     Document Type: Article

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26. 4, filtered, and concentrated under vacuum. The crude oil was purified by silica gel flash chromatography to give the desired product.
27. The reaction of methyl benzoylacetate and 3,4-dichlorobenzaldehyde with NFSI in nitroethane proceeded by way of a Lewis acid-catalyzed Knoevenagel condensation/Nazarov cyclization/fluorination sequence to afford fluorinated 1-indanone derivative in 62% yield with high diastereoselectivity (trans/cis: 25/1). The electrophilic fluorination trapping as a terminating step for Nazarov cyclization may facilitate catalyst turnover.
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30. 4, filtered, and concentrated under vacuum. The crude oil was purified by silica gel flash chromatography to give the desired product.