Ene-like addition of an oxoammonium cation to alkenes: highly selective route to allylic alkoxyamines

Priya P Pradhan; James M Bobbitt; William F Bailey

doi:10.1021/ol062196z

Ene-like addition of an oxoammonium cation to alkenes: highly selective route to allylic alkoxyamines

Org Lett. 2006 Nov 23;8(24):5485-7. doi: 10.1021/ol062196z.

Authors

Priya P Pradhan¹, James M Bobbitt, William F Bailey

Affiliation

¹ Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, USA.

PMID: 17107053
DOI: 10.1021/ol062196z

Abstract

The oxoammonium cation of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) adds rapidly at room temperature in an ene-like fashion to trisubstituted alkenes to afford allylic alkoxyamines in high yield. [reaction: see text]

Publication types

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

MeSH terms

Alkenes / chemistry*
Amines / chemical synthesis*
Cations / chemistry*
Indicators and Reagents
Magnetic Resonance Spectroscopy
Quaternary Ammonium Compounds / chemistry*

Substances

Alkenes
Amines
Cations
Indicators and Reagents
Quaternary Ammonium Compounds