Au(I)-Catalyzed Synthesis of Trisubstituted Indolizines
from 2‑Propargyloxypyridines and Methyl Ketones

Rossler, Matthew
D.; Hartgerink, Colin T.; Zerull, Emily E.; Boss, Benjamin L.; Frndak, Abigail K.; Mason, Miles M.; Nickerson, Leslie A.; Romero, Evan O.; Van de Burg, Jaimie E.; Staples, Richard J.; Anderson, Carolyn E.

doi:10.1021/acs.orglett.9b01929.s001

ol9b01929_si_001.pdf (11.09 MB)

Au(I)-Catalyzed Synthesis of Trisubstituted Indolizines from 2‑Propargyloxypyridines and Methyl Ketones

journal contribution

posted on 2019-07-01, 18:41 authored by Matthew D. Rossler, Colin T. Hartgerink, Emily E. Zerull, Benjamin L. Boss, Abigail K. Frndak, Miles M. Mason, Leslie A. Nickerson, Evan O. Romero, Jaimie E. Van de Burg, Richard J. Staples, Carolyn E. Anderson

A new Au(I)-catalyzed method for the preparation of trisubstituted indolizines from easily accessible 2‑propargyloxy-pyridines is reported. The reaction tolerates a wide range of functionality, allowing for diversity to be introduced in four distinct regions of the product (R, R¹, R², and Ar). The proposed mechanism proceeds via enol addition to an allenamide intermediate and explains the observed increase in yields when electron poor methyl ketones are utilized.