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: Modular and stereoselective synthesis of tetrasubstituted helical alkenes via a palladium-catalyzed domino reaction.
    Author: Liu H, El-Salfiti M, Chai DI, Auffret J, Lautens M.
    Journal: Org Lett; 2012 Jul 20; 14(14):3648-51. PubMed ID: 22738660.
    Abstract:
    A highly modular and stereoselective synthesis of tetrasubstituted helical alkenes is accomplished by a Pd-catalyzed norbornene-mediated domino reaction. This protocol features the rapid assembly of four C-C bonds via sequential C-H activations and carbopalladations along with efficient access to enantiopure bromoalkyl aryl alkyne precursors using homologative alkynylation as the key transformation. Three distinct elements of stereoselectivity were observed in the preparation of the chiral helical alkenes: retention of stereochemistry of the substrates, induced helical diastereoselectivity in the alkene formation, and the exclusive exo-facial selectivity of the norbornene incorporation.
    [Abstract] [Full Text] [Related] [New Search]