Au(I)-Catalyzed Synthesis of Trisubstituted Indolizines
from 2‑Propargyloxypyridines and Methyl Ketones
Posted on 2019-07-01 - 18:41
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.
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Rossler, Matthew
D.; Hartgerink, Colin T.; Zerull, Emily E.; Boss, Benjamin L.; Frndak, Abigail K.; Mason, Miles M.; et al. (2019). Au(I)-Catalyzed Synthesis of Trisubstituted Indolizines
from 2‑Propargyloxypyridines and Methyl Ketones. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b01929
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AUTHORS (11)
MR
Matthew
D. Rossler
CH
Colin T. Hartgerink
EZ
Emily E. Zerull
BB
Benjamin L. Boss
AF
Abigail K. Frndak
MM
Miles M. Mason
LN
Leslie A. Nickerson
ER
Evan O. Romero
JV
Jaimie E. Van de Burg
RS
Richard J. Staples
CA
Carolyn E. Anderson