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Enantioselective allylations of selected alpha, beta, gamma, delta-unsaturated aldehydes by axially chiral N,N'-dioxides. Synthesis of the left-hand part of papulacandin D
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SYSNO ASEP 0471657 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Enantioselective allylations of selected alpha, beta, gamma, delta-unsaturated aldehydes by axially chiral N,N'-dioxides. Synthesis of the left-hand part of papulacandin D Author(s) Vlašaná, K. (CZ)
Betík, R. (CZ)
Valterová, Irena (UOCHB-X) RID, ORCID
Nečas, D. (CZ)
Kotora, M. (CZ)Source Title Current Organocatalysis - ISSN 2213-3372
Roč. 3, č. 3 (2016), s. 301-305Number of pages 5 s. Language eng - English Country NL - Netherlands Keywords allylation ; aldehyde ; Lewis base ; asymmetric synthesis ; organocatalysis ; homoallylic alcohols Subject RIV CC - Organic Chemistry OECD category Organic chemistry Institutional support UOCHB-X - RVO:61388963 UT WOS 000406981800008 DOI 10.2174/2213337203666160304193640 Annotation Allylations of several structurally different alpha, beta, gamma, delta-aldehydes were carried out in various solvents in the presence of a catalytic amount of an N,N’-dioxide to access conditions leading to the highest symmetric induction. Out of screening of several reaction conditions the highest asymmetric induction (up to 98% ee) was achieved in THF. A higher asymmetric induction was observed with substrates bearing additional substituents on alpha-carbon atom. Allylation of (S)-(2E,4E)-2,8-dimethyldecadienal gave rise to the corresponding homoallylic alcohol with a high asymmetric induction of 92% ee. The method is useful for synthesis of valuable building block for organic synthesis as it was demonstrated by a synthesis of a papulacandin D intermediate. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2017
Number of the records: 1