Enantioselective fluoroamination: 1,4-addition to conjugated dienes using anionic phase-transfer catalysis

Hunter P Shunatona; Natalja Früh; Yi-Ming Wang; Vivek Rauniyar; F Dean Toste

doi:10.1002/anie.201302002

Enantioselective fluoroamination: 1,4-addition to conjugated dienes using anionic phase-transfer catalysis

Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7724-7. doi: 10.1002/anie.201302002. Epub 2013 Jun 13.

Authors

Hunter P Shunatona¹, Natalja Früh, Yi-Ming Wang, Vivek Rauniyar, F Dean Toste

Affiliation

¹ Department of Chemistry, University of California-Berkeley, Latimer Hall, Berkeley, CA, USA.

PMID: 23766145
DOI: 10.1002/anie.201302002

Abstract

Chiral-anion phase-transfer catalysis (PTC) has been applied towards the enantioselective fluorocyclization reactions of 1,3-dienes. The method affords unprecedented fluorinated benz[f]isoquinoline and octahydroisoquinoline products in high yields and up to 96 % ee. New fluorinated amine reagents outperformed Selectfluor in the desired transformation.

Keywords: amination; asymmetric catalysis; cyclization; fluorine; phase-transfer catalysis.