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Volumn 47, Issue 36, 2008, Pages 6873-6876

Catalytic enantioselective alkylation of substituted dioxanone enol ethers: ready access to C(α)-tetrasubstituted hydroxyketones, acids,and esters

Author keywords

Alcohols; Allylic compounds; Asymmetric catalysis; Enantioselectivity; Palladium

Indexed keywords

ACIDS; ALKYLATION; ESTERIFICATION; ESTERS; ETHERS; HYDROCARBONS; KETONES; ORGANIC COMPOUNDS; PALLADIUM; RAW MATERIALS; SYNTHESIS (CHEMICAL);

EID: 52449089307     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801424     Document Type: Article
Times cited : (67)

References (54)
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    • For an alternative approach to asymmetric enolate alkylation, see: a
    • For an alternative approach to asymmetric enolate alkylation, see: a) M. Braun, F. Laicher, T. Meier, Angew. Chem. 2000, 112, 3637-3640;
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    • For the use of dioxanones as a template for the synthesis of stereochemically rich substrances, see: a, Eds: D. Enders, K.-E. Jaeger, Wiley-VCH, Weinheim
    • For the use of dioxanones as a template for the synthesis of stereochemically rich substrances, see: a) D. Enders, W. Bettray in Asymmetric Synthesis with Chemical and Biological Methods (Eds: D. Enders, K.-E. Jaeger), Wiley-VCH, Weinheim, 2007, pp. 38-75;
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    • Silyl enol ethers were formed from alkylated ketones. The alkylated ketone was treated with triethylsilyl chloride (1.3 equiv), triethylamine (1.6 equiv), and sodium iodide (1.3 equiv)in acetonitrile (0.63M) and isolated by silica gel chromatography in 46-78% yield, with 6-15% yield of the isomeric enol ether. For details, see the Supporting Information.
    • Silyl enol ethers were formed from alkylated ketones. The alkylated ketone was treated with triethylsilyl chloride (1.3 equiv), triethylamine (1.6 equiv), and sodium iodide (1.3 equiv)in acetonitrile (0.63M) and isolated by silica gel chromatography in 46-78% yield, with 6-15% yield of the isomeric enol ether. For details, see the Supporting Information.
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    • and references therein
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    • See Supporting Information for details
    • See Supporting Information for details.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.