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

Search MEDLINE/PubMed


  • Title: Stereoselective synthesis of chiral 4-(1-chloroalkyl)-beta-lactams starting from amino acids and their transformation into functionalized chiral azetidines and pyrrolidines.
    Author: Dekeukeleire S, D'hooghe M, Törnroos KW, De Kimpe N.
    Journal: J Org Chem; 2010 Sep 03; 75(17):5934-40. PubMed ID: 20704284.
    Abstract:
    Chiral short-chain alpha-chloroaldehydes were prepared starting from enantiomerically pure amino acids in a three-step approach, thus providing a practical synthetic alternative for known organocatalytic alpha-chlorination procedures. The latter aldehydes proved to be useful starting materials for the stereoselective Staudinger synthesis of (3S,4S)-4-[(1S)-1-chloroalkyl]azetidin-2-ones in high diastereomeric ratios and good overall yields, which were used as chiral building blocks for the preparation of a number of azetidines and pyrrolidines.
    [Abstract] [Full Text] [Related] [New Search]