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  • Title: Tetrazolic acid functionalized dihydroindol: rational design of a highly selective cyclopropanation organocatalyst.
    Author: Hartikka A, Arvidsson PI.
    Journal: J Org Chem; 2007 Jul 20; 72(15):5874-7. PubMed ID: 17585815.
    Abstract:
    Herein we wish to report our development of an improved catalyst (S)-(-)-indoline-2-yl-1H-tetrazole (1) for the enantioselective organocatalyzed cyclopropanation of alpha,beta-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 alpha,beta-unsaturated aldehydes. The new catalyst provides the best results so far reported for intermolecular enantioselective organocatalyzed cyclopropanation.
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