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Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones.
Org Lett. 2020 06 05; 22(11):4272-4275.OL

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.

Authors+Show Affiliations

Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.Small Molecule Process Chemistry, Genentech, Inc., 1 DNA Way, South San Francisco, California 94080, United States.Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

32422045

Citation

Lavernhe, Remi, et al. "Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones." Organic Letters, vol. 22, no. 11, 2020, pp. 4272-4275.
Lavernhe R, Alexy EJ, Zhang H, et al. Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. Org Lett. 2020;22(11):4272-4275.
Lavernhe, R., Alexy, E. J., Zhang, H., & Stoltz, B. M. (2020). Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. Organic Letters, 22(11), 4272-4275. https://doi.org/10.1021/acs.orglett.0c01303
Lavernhe R, et al. Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. Org Lett. 2020 06 5;22(11):4272-4275. PubMed PMID: 32422045.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones. AU - Lavernhe,Remi, AU - Alexy,Eric J, AU - Zhang,Haiming, AU - Stoltz,Brian M, Y1 - 2020/05/18/ PY - 2020/5/19/pubmed PY - 2021/7/1/medline PY - 2020/5/19/entrez SP - 4272 EP - 4275 JF - Organic letters JO - Org Lett VL - 22 IS - 11 N2 - 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. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/32422045/Palladium_Catalyzed_Enantioselective_Decarboxylative_Allylic_Alkylation_of_Acyclic_α_N_Pyrrolyl/Indolyl_Ketones_ L2 - https://doi.org/10.1021/acs.orglett.0c01303 DB - PRIME DP - Unbound Medicine ER -