Published June 5, 2020
| Accepted Version + Supplemental Material
Journal Article
Open
Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones
Abstract
The synthesis of fully substituted α-N-pyrrolyl and indolyl ketones via enantioselective palladium-catalyzed allylic alkylation is described. The acyclic ketones are alkylated in high yields with high enantioselectivities through the use of an electron-deficient phosphinooxazoline ligand, furnishing a highly congested and synthetically challenging stereocenter. The obtained alkylation products contain multiple reactive sites poised for additional functionalizations and diversification.
Additional Information
© 2020 American Chemical Society. Received: April 14, 2020; Published: May 18, 2020. We thank the NIH-NIGMS (R01GM080269), the Gordon and Betty Moore Foundation, and Caltech for financial support. E.J.A. thanks the National Science Foundation for a predoctoral fellowship. We thank Dr. David VanderVelde (Caltech) for NMR expertise. Dr. Scott Virgil (Caltech Center for Catalysis and Chemical Synthesis) is thanked for instrumentation and SFC assistance. Dr. Michael Takase (Caltech) and Lawrence Henling (Caltech) are acknowledged for X-ray analysis. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms-1637388.pdf
Supplemental Material - ol0c01303_si_001.pdf
Files
nihms-1637388.pdf
Files
(12.2 MB)
| Name | Size | Download all |
|---|---|---|
|
md5:5b49e0e8f58929ebd6554aa7f7e738bf
|
1.1 MB | Preview Download |
|
md5:5b803c8e30984ceab22140b661e74944
|
11.1 MB | Preview Download |
Additional details
- PMCID
- PMC7608871
- Eprint ID
- 103305
- DOI
- 10.1021/acs.orglett.0c01303
- Resolver ID
- CaltechAUTHORS:20200519-093555551
- NIH
- R01GM080269
- Gordon and Betty Moore Foundation
- Caltech
- NSF Predoctoral Fellowship
- Created
-
2020-05-19Created from EPrint's datestamp field
- Updated
-
2022-02-09Created from EPrint's last_modified field