Synthesis of New Chiral Pincer-Complex Catalysts for Asymmetric Allylation of Sulfonimines
Stockholm University, Faculty of Science, Department of Organic Chemistry2006 (English)In: Inorganica Chimica Acta, ISSN 0020-1693, Vol. 359, no 6, 1767-1772 p.Article in journal (Refereed) Published
Four new chiral pincer-complexes were prepared based on coupling of BINOL and TADDOL moieties with iodoresorcinol followed by oxidative addition of palladium(0). The X-ray analysis of complex 5a revealed that the BINOL rings form a well-defined chiral pocket around the palladium atom. This chiral environment can be further modified by γ-substitution of the BINOL rings. Preliminary studies for electrophilic allylation of sulfonimine 2 with allylstannane revealed that the presented chiral complexes are promising asymmetric catalysts for preparation of chiral homoallyl amines. The best result was achieved employing catalytic amounts of γ-Me BINOL complex 6 affording homoallyl amine 4 with 59% ee and 74% isolated yield.
Place, publisher, year, edition, pages
2006. Vol. 359, no 6, 1767-1772 p.
IdentifiersURN: urn:nbn:se:su:diva-25326DOI: 10.1016/j.ica.2005.06.059OAI: oai:DiVA.org:su-25326DiVA: diva2:199474
Part of urn:nbn:se:su:diva-8042006-01-182006-01-182009-05-19Bibliographically approved