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Enantioselective Allylation of Aldehydes Catalyzed by Diasteroisomeric Bis(tetrahydroisoquinoline) N, N'-Dioxides
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SYSNO ASEP 0353857 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Enantioselective Allylation of Aldehydes Catalyzed by Diasteroisomeric Bis(tetrahydroisoquinoline) N, N'-Dioxides Author(s) Vlašaná, K. (CZ)
Hrdina, R. (CZ)
Valterová, Irena (UOCHB-X) RID, ORCID
Kotora, M. (CZ)Number of authors 4 Source Title European Journal of Organic Chemistry - ISSN 1434-193X
-, č. 36 (2010), s. 7040-7044Number of pages 5 s. Language eng - English Country DE - Germany Keywords organocatalysis ; allylation ; asymmetric catalysis ; Lewis bases Subject RIV CC - Organic Chemistry CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000285311000021 DOI 10.1002/ejoc.201001219 Annotation The course of enantioselective allylation of aromatic and alpha, beta-unsaturated aldehydes with allyltrichlorosilane catalyzed by two diastereoisomeric (R,Rax,R)- and (R,Sax,R)-bis-1,1-[5,6,7,8-tetrahydro- 3-(tetrahydrofuran-2-yl)isoquinoline] N,N-dioxides was influenced by the solvent. The (R,Sax,R) catalyst efficiently promoted the reaction in THF with enantioselectivity up to 96%. On the other hand, the allylation of aromatic aldehydes in the presence of the (R,Rax,R) catalyst proceeded only in MeCN (up to 67%ee). The allylation of alpha, beta- unsaturated aldehydes proceeded only in dichloromethane (enantioselectivity up to 68%). Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2011
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