Enantioselective Allylation of Aldehydes Catalyzed by Diasteroisomeric Bis(tetrahydroisoquinoline) N, N'-Dioxides

0353857 - ÚOCHB 2011 RIV DE eng J - Článek v odborném periodiku
Vlašaná, K. - Hrdina, R. - Valterová, Irena - Kotora, M.
Enantioselective Allylation of Aldehydes Catalyzed by Diasteroisomeric Bis(tetrahydroisoquinoline) N, N'-Dioxides.
European Journal of Organic Chemistry. -, č. 36 (2010), s. 7040-7044. ISSN 1434-193X. E-ISSN 1099-0690
Grant ostatní: GA ČR(CZ) GA203/08/0350; GA MŠk(CZ) LC06070
Program: LC
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: organocatalysis * allylation * asymmetric catalysis * Lewis bases
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.206, rok: 2010

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%).
Trvalý link: http://hdl.handle.net/11104/0192986