Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition

Andrew G Lohse; Richard P Hsung

doi:10.1021/ol901283m

Thermal intramolecular [4 + 2] cycloadditions of allenamides: a stereoselective tandem propargyl amide isomerization-cycloaddition

Org Lett. 2009 Aug 6;11(15):3430-3. doi: 10.1021/ol901283m.

Authors

Andrew G Lohse¹, Richard P Hsung

Affiliation

¹ Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, USA.

Abstract

A stereoselective intramolecular normal demand [4 + 2] cycloaddition of allenamides under thermal conditions without metal assistance is described. This work led to the development of a stereoselective tandem propargyl amide-isomerization-[4 + 2] cycloaddition sequence amenable for rapid assembly of complex nitrogen heterocycles.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Amides / chemistry*
Crystallography, X-Ray
Cyclization
Heterocyclic Compounds / chemical synthesis*
Heterocyclic Compounds / chemistry
Stereoisomerism

Substances

Amides
Heterocyclic Compounds

Abstract

Publication types

MeSH terms

Substances

Grants and funding