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: Use of an aminosilyllithium for the diastereoselective synthesis of diphenyl oxasilacyclopentane acetals and polyols.
    Author: Tenenbaum JM, Woerpel KA.
    Journal: Org Lett; 2003 Nov 13; 5(23):4325-7. PubMed ID: 14601991.
    Abstract:
    [reaction: see text] The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.
    [Abstract] [Full Text] [Related] [New Search]