Enantioselective Silver-Catalyzed Cascade Synthesis of Fused Lactone and Lactam Oxazolines

Raquel de la Campa; Rubén Manzano; Paul Calleja; Sam R Ellis; Darren J Dixon

doi:10.1021/acs.orglett.8b02383

Enantioselective Silver-Catalyzed Cascade Synthesis of Fused Lactone and Lactam Oxazolines

Org Lett. 2018 Oct 5;20(19):6033-6036. doi: 10.1021/acs.orglett.8b02383. Epub 2018 Sep 17.

Authors

Raquel de la Campa¹, Rubén Manzano¹, Paul Calleja¹, Sam R Ellis¹, Darren J Dixon¹

Affiliation

¹ Department of Chemistry, Chemistry Research Laboratory , University of Oxford , 12 Mansfield Road , Oxford OX1 3TA , U.K.

PMID: 30221522
DOI: 10.1021/acs.orglett.8b02383

Abstract

A new and highly stereoselective cascade reaction between isocyanoacetate esters and α-hydroxy and α-amino ketones has been developed. A cinchona alkaloid derived aminophosphine/silver(I) catalyst complex promoted the reaction and enabled the ready synthesis of fused bicyclic γ-lactone and γ-lactam oxazolines with high enantiocontrol (up to 99% ee).

Publication types

Research Support, Non-U.S. Gov't