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Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group.
Org Lett. 2017 09 01; 19(17):4424-4427.OL

Abstract

An efficient and stereospecific Pd-catalyzed protocol for the C-H arylation of pyroglutamic acid derivatives that uses 8-aminoquinoline as a directing group is described. The reaction was shown to proceed efficiently with a variety of aryl and heteroaryl iodides bearing different functional groups, giving C3-arylated cis products in good to high yields. Removal of the 8-aminoquinoline unit from these C-H arylation products enables access to synthetically useful cis and trans pyroglutamic acid-based building blocks.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Verho O
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States. Broad Institute , Cambridge, Massachusetts 02142, United States.
Maetani M
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States. Broad Institute , Cambridge, Massachusetts 02142, United States.
Melillo B
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States. Broad Institute , Cambridge, Massachusetts 02142, United States.
Zoller J
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States. Broad Institute , Cambridge, Massachusetts 02142, United States.
Schreiber SL
Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States. Broad Institute , Cambridge, Massachusetts 02142, United States.

MeSH

AminoquinolinesCatalysisMolecular StructurePalladiumPyrrolidonecarboxylic AcidStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

28809506

Citation

Verho, Oscar, et al. "Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled By 8-Aminoquinoline as a Directing Group." Organic Letters, vol. 19, no. 17, 2017, pp. 4424-4427.
Verho O, Maetani M, Melillo B, et al. Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group. Org Lett. 2017;19(17):4424-4427.
Verho, O., Maetani, M., Melillo, B., Zoller, J., & Schreiber, S. L. (2017). Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group. Organic Letters, 19(17), 4424-4427. https://doi.org/10.1021/acs.orglett.7b01776
Verho O, et al. Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled By 8-Aminoquinoline as a Directing Group. Org Lett. 2017 09 1;19(17):4424-4427. PubMed PMID: 28809506.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereospecific Palladium-Catalyzed C-H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group. AU - Verho,Oscar, AU - Maetani,Micah, AU - Melillo,Bruno, AU - Zoller,Jochen, AU - Schreiber,Stuart L, Y1 - 2017/08/15/ PY - 2017/8/16/pubmed PY - 2018/9/13/medline PY - 2017/8/16/entrez SP - 4424 EP - 4427 JF - Organic letters JO - Org Lett VL - 19 IS - 17 N2 - An efficient and stereospecific Pd-catalyzed protocol for the C-H arylation of pyroglutamic acid derivatives that uses 8-aminoquinoline as a directing group is described. The reaction was shown to proceed efficiently with a variety of aryl and heteroaryl iodides bearing different functional groups, giving C3-arylated cis products in good to high yields. Removal of the 8-aminoquinoline unit from these C-H arylation products enables access to synthetically useful cis and trans pyroglutamic acid-based building blocks. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/28809506/Stereospecific_Palladium_Catalyzed_C_H_Arylation_of_Pyroglutamic_Acid_Derivatives_at_the_C3_Position_Enabled_by_8_Aminoquinoline_as_a_Directing_Group_ L2 - https://doi.org/10.1021/acs.orglett.7b01776 DB - PRIME DP - Unbound Medicine ER -