Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes

Anirudra Paul; N R Thimmegowda; Thiago Galani Cruz; Daniel Seidel

doi:10.1021/acs.orglett.7b03721

Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes

Org Lett. 2018 Feb 2;20(3):602-604. doi: 10.1021/acs.orglett.7b03721. Epub 2018 Jan 12.

Authors

Anirudra Paul^{1

2}, N R Thimmegowda¹, Thiago Galani Cruz¹, Daniel Seidel^{1

2}

Affiliations

¹ Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.
² Center for Heterocyclic Compounds, Department of Chemistry, University of Florida , Gainesville, Florida 32611, United States.

Abstract

Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and β-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Aldehydes / chemistry*
Amino Acids
Ketones
Molecular Structure
Proline

Substances

Aldehydes
Amino Acids
Ketones
Proline

Grants and funding

R01 GM101389/GM/NIGMS NIH HHS/United States