Organic Letters
Organic Letters
4 years ago

Stereospecific Palladium-Catalyzed C–H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group

Stereospecific Palladium-Catalyzed C–H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group
Micah Maetani, Stuart L. Schreiber, Jochen Zoller, Bruno Melillo, Oscar Verho
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01776

DOI: 10.1021/acs.orglett.7b01776

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