An Enantiodivergent Synthesis of C^α-Methyl Nipecotic Acid Analogues From δ-Lactam Derivatives Obtained Through a Highly Stereoselective Cyclization Strategy

Authors

Souvik Banerjee, University of Southern Mississippi
Emily R. Vogel, University of Southern Mississippi
Daniel Hinton, University of Southern Mississippi
Michael Sterling, University of Southern Mississippi
Douglas S. Masterson, University of Southern MississippiFollow

Document Type

Article

Publication Date

12-1-2015

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Abstract

A stereoselective and enantiodivergent strategy for the construction of δ-lactams is described. The strategy utilizes chiral malonic esters prepared from enantiomerically enriched mono esters of disubstituted malonic acid. A cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. The resulting δ-lactams are then converted into nipecotic acid analogues using straightforward transformations. The resulting nipecotic acid analogues proved capable organocatalysts in Mannich reactions.

Comments

© This manuscript version is made available under the CC-BY-NC-ND 4.0 license https://creativecommons.org/licenses/by-nc-nd/4.0/.

Publication Title

Tetrahedron Asymmetry

Volume

26

Issue

21-22

First Page

1292

Last Page

1299

Recommended Citation

Banerjee, S., Vogel, E., Hinton, D., Sterling, M., Masterson, D. (2015). An Enantiodivergent Synthesis of C^α-Methyl Nipecotic Acid Analogues From δ-Lactam Derivatives Obtained Through a Highly Stereoselective Cyclization Strategy. Tetrahedron Asymmetry, 26(21-22), 1292-1299.
Available at: https://aquila.usm.edu/fac_pubs/18645