Asymmetric Catalysis in a Micro Reactor: Ce, Yb and Lu Catalysed Enantioselective Addition of Trimethylsilyl Cyanide to Benzaldehyde
2004 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 46, 10515-10520 p.Article in journal (Refereed) Published
A T-shaped micro reactor was used for the optimisation of reaction conditions for the enantioselective silyleyanation of benzaldehyde catalysed by lanthanide-pybox complexes. Compared to a conventional batch procedure, higher conversion was observed within shorter reaction time. The micro reactor process involving Lu(III) afforded essentially the same enantioselectivity as the batch process (73 vs 76% ee), whereas the enantioselectivity was lower in the micro reactor for catalysts containing Yb(III) (53 compared to 72%). Ce(III) provided very low selectivity in both types of processes (1 and 11 % ee, respectively). A study of the effect of additives showed that the enantioselectivity in the Yb catalysed reaction performed in the micro reactor could be increased to 66%, whereas only a minor improvement, to 78% ee, was observed in the reaction with Lu.
Place, publisher, year, edition, pages
2004. Vol. 60, no 46, 10515-10520 p.
Asymmetric metal catalysis; Lanthanide; Micro reactor; Pybox; Silylcyanations; benzaldehyde; cerium; cyanide; lanthanide; lutetium; trimethylsilyl derivative; ytterbium; addition reaction; article; asymmetric catalysis; catalyst; chemical analysis; chemical structure; cyanation; enantioselectivity; priority journal; reaction analysis; reactor; structure analysis
IdentifiersURN: urn:nbn:se:kth:diva-6919DOI: 10.1016/j.tet.2004.08.080ISI: 000224632300015ScopusID: 2-s2.0-4944237872OAI: oai:DiVA.org:kth-6919DiVA: diva2:11766
QC 20100809 QC 201109162007-03-222007-03-222011-09-16Bibliographically approved