Literature DB >> 30011353

Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles.

Kevin J Schwarz1, Chao Yang1, James W B Fyfe1, Thomas N Snaddon1.   

Abstract

The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Lewis bases; benzylation; cooperative catalysis; enantioselectivity; palladium

Mesh：

Substances：

Year:  2018        PMID： 30011353      PMCID： PMC6499373          DOI： 10.1002/anie.201806742

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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