These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Direct carbon-carbon bond formation via soft enolization: a biomimetic asymmetric Mannich reaction of phenylacetate thioesters.
    Author: Kohler MC, Yost JM, Garnsey MR, Coltart DM.
    Journal: Org Lett; 2010 Aug 06; 12(15):3376-9. PubMed ID: 20608684.
    Abstract:
    An asymmetric Mannich reaction of phenylacetate thioesters and sulfonylimines using cinchona alkaloid-based amino (thio)urea catalysts is reported that employs proximity-assisted soft enolization. This approach to enolization is based on the cooperative action of a carbonyl-activating hydrogen bonding (thio)urea moiety and an amine base contained within a single catalytic entity to facilitate intracomplex deprotonation. Significantly, this allows thioesters over a range of acidity to react efficiently, thereby opening the door to the development of a general mode of enolization-based organocatalysis of monocarboxylic acid derivatives.
    [Abstract] [Full Text] [Related] [New Search]