Lewis acid catalyzed α-functionalization of ketals for the regioselective synthesis of α-carbamoyl ketals

Philip Magnus; Alec J Brozell

doi:10.1021/ol301710w

Lewis acid catalyzed α-functionalization of ketals for the regioselective synthesis of α-carbamoyl ketals

Org Lett. 2012 Aug 3;14(15):3952-4. doi: 10.1021/ol301710w. Epub 2012 Jul 19.

Authors

Philip Magnus¹, Alec J Brozell

Affiliation

¹ Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, Texas 78712-1167, USA. p.magnus@mail.utexas.edu

PMID: 22812432
DOI: 10.1021/ol301710w

Abstract

Treatment of 1 with DEAD in the presence of BF(3)·OEt(2) gave 2 (R = H), which was N-alkylated to give 2 (R = CH(2)CO(2)Et), and insitu eliminated (E1cb) to give α-carbamoyl ketals.