Tetrahydroisoquinoline-Based N-Oxides as Chiral Organocatalysts for the Asymmetric Allylation of Aldehydes
2011 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 2011, no 34, 6923-6932 p.Article in journal (Refereed) Published
The short synthesis of a series of novel chiral N-oxideorganocatalysts and their evaluation in the asymmetric allylation reaction of aromatic and α-β-unsaturated aldehydes with allyltrichlorosilane is reported. These readily modifiable organocatalysts are the first of their kind based on the tetrahydroisoquinoline framework. The chiral homoallyl products were obtained with good chemical efficiency (up to 93 % yield) and high enantioselectivity (up to 91 % ee) under mild reaction conditions (23 °C).
Place, publisher, year, edition, pages
2011. Vol. 2011, no 34, 6923-6932 p.
Organocatalysis, Allylation, Heterocycles, Aldehydes, Lewis bases, Tetrahydroisoquinoline
Research subject Organic Pharmaceutical Chemistry
IdentifiersURN: urn:nbn:se:uu:diva-165365DOI: 10.1002/ejoc.201100923ISI: 000297205800013OAI: oai:DiVA.org:uu-165365DiVA: diva2:473135