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Synthesis of Ester-Substituted Indolizines from 2-Propargyloxypyridines and 1,3-Dicarbonyls

Carolyn E. Anderson*, Haleigh I. Bos, Daniel M. Dreher, Colin T. Hartgerink, Chase J. Scholtens and Richard J. Staples

*Department of Chemistry and Biochemistry, Calvin University, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546, United States, Email:

C. E. Anderson, H. I. Bos, D. M. Dreher, C. T. Hartgerink, C. J. Scholtens, R. J. Staples, J. Org. Chem., 2022, 87, 10241-10249.

DOI: 10.1021/acs.joc.2c01219

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Two complementary Au(I)-catalyzed methods provide ester-substituted indolizines from easily accessible 2-propargyloxypyridines and either acetoacetates or dimethyl malonate. These reactions tolerate a wide range of functionality, allowing for diversification at three distinct positions of the product.

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proposed mechanism

Key Words


ID: J42-Y2022