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Volumn , Issue 9, 2007, Pages 1441-1445

Development of the first Brønsted acid assisted enantioselective Brønsted acid catalyzed direct Mannich reaction

Author keywords

BINOL phosphate; Bro nsted acid; Cooperative catalysis; Mannich reaction; Organocatalysis

Indexed keywords

2,2' DIHYDROXY 1,1' BINAPHTHYL; ACETOPHENONE; ALDIMINE DERIVATIVE; BETA AMINO KETONE DERIVATIVE; BRONSTED ACID; IMINE; KETONE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34250760386     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980369     Document Type: Article
Times cited : (89)

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    • General Procedure for Direct Mannich Reaction In a typical experiment acetophenone 3 (2 equiv, aldimine 2, catalyst 1c (10 mol, and AcOH (20 mol, were suspended in Bu2O in a screw-capped vial and the resulting mixture was allowed to stir at r.t. for 60 h. Purification of the crude product by column chromatography on silica gel afforded the corresponding product 4. 3-(4-Chlorophenylamino)-1,3- diphenylpropan-1-one (4a) The title compound was isolated by column chromatography (n-hexane-EtOAc, 10:1) as a colorless solid in 43% yield and 86% ee. The ee was determined by HPLC using Chiralcel OD-H column [n-hexane-i-PrOH (90:10, flow rate 0.6 mL/min; major enantiomer: tR, 25.3 min; minor enantiomer: tR, 28.2 min, mp 162°C; [α]D +31.0 (c 1.0, CH 2Cl2, IRKBR, 3373, 2924, 1666, 1507, 1489, 1286, 1003, 820, 703 cm-1. ESI-HRM
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.