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The First Catalytic Asymmetric Allylation of Imines With the tetraallylsilane-TBAF-MeOH System, Using the Chiral Bis-Pi-Allylpalladium Complex

The First Catalytic Asymmetric Allylation of Imines With the tetraallylsilane-TBAF-MeOH System, Using the Chiral Bis-Pi-Allylpalladium Complex

Rodney A Fernandes, Yoshinori Yamamoto

J Org Chem. 2004 Feb 6;69(3):735-8.

PMID: 14750798

Abstract:

The asymmetric allylation of imines with use of catalytic transition metals with chiral ligands should be a new frontier of the enantioselective C-C bond formation. So far allyltrimethylsilane, allyltrichlorosilane, and allyltrimethoxysilane have been commonly employed with use of either silane activators or dual silane-imine activators. However, tetraallylsilane is untouched in the allylation of aldimines. The first allylation of aldimines with the tetraallylsilane-TBAF-MeOH system with use of the bis-pi-allylpalladium catalyst under catalytic, non-Lewis acid, essentially neutral and very mild reaction conditions has been achieved. The reaction is triggered by dual activation/promotion by TBAF and MeOH in which the fluoride anion activates the C-Si bond cleavage and MeOH promotes the facile protonation of intermediate palladium amide. Thus, the synthesis of chiral homoallylamines is achieved in a shorter reaction time and higher yields and enantioselectivities through an efficient, general, and reproducible allylation protocol for imines.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1112669	Tetraallylsilane		1112-66-9	Price

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