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: Palladium-catalyzed asymmetric synthesis of axially chiral (allenylmethyl)silanes and chirality transfer to stereogenic carbon centers in S(E)' reactions.
    Author: Ogasawara M, Ueyama K, Nagano T, Mizuhata Y, Hayashi T.
    Journal: Org Lett; 2003 Jan 23; 5(2):217-9. PubMed ID: 12529144.
    Abstract:
    [reaction: see text] Novel stereoselective reactions of 4-substituted-1-trimethylsilyl-2,3-butadienes ((allenylmethyl)silanes) were developed. The axially chiral (allenylmethyl)silanes were prepared from (3-bromopenta-2,4-dienyl)trimethylsilane by a Pd-catalyzed asymmetric reaction with soft nucleophiles with up to 88% enantioselectivity. The (allenylmethyl)silanes reacted with acetals in the presence of a TiCl(4) promoter to give 1,3-diene derivatives via an S(E)' pathway. The 1,3-dienyl products have (E)-geometry exclusively and up to 88%( )()chirality transfer from the axially chiral allenes to the centrally chiral 1,3-dienes was observed in the S(E)' reaction.
    [Abstract] [Full Text] [Related] [New Search]