Tetrazolic Acid Functionalized Dihydroindol: Rational Design of a Highly Selective Cyclopropanation Organocatalyst
2007 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 15, 5874-5877 p.Article in journal (Refereed) Published
Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of α,β-unsaturated aldehydes with sulfur ylides. The new organocatalyst readily facilitates the enantioselective organocatalytic cyclopropanation, providing cyclized product in excellent diastereoselectivities ranging from 96% to 98% along with enantioselectivities exceeding 99% enantiomeric excess for all reacted α,β-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.
Place, publisher, year, edition, pages
2007. Vol. 72, no 15, 5874-5877 p.
Nitrogen heterocycle, Diastereoselectivity, Cyclization, Ylide, Organic sulfide, Aldehyde, Unsaturated compound, Enantioselectivity, Tetrazole derivatives, Enantiomeric excess, Catalyst, Cyclopropanation, Selectivity, Indole derivatives, Functionalization
IdentifiersURN: urn:nbn:se:uu:diva-95940DOI: 10.1021/jo070519eISI: 000247992800059OAI: oai:DiVA.org:uu-95940DiVA: diva2:170327