Regio- and Stereoselective Palladium-Catalyzed C(sp3)–H Arylation of Pyrrolidines and Piperidines with C(3) Directing Groups | Zendy

Daniele Antermite | Zendy; Dominic P. Affron | Zendy; James A. Bull | Zendy

Open Access

Regio- and Stereoselective Palladium-Catalyzed C(sp³)–H Arylation of Pyrrolidines and Piperidines with C(3) Directing Groups

Author(s) -

Daniele Antermite,

Dominic P. Affron,

James A. Bull

Publication year - 2018

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.8b01521

Subject(s) - chemistry , stereoselectivity , catalysis , amide , palladium , base (topology) , alcohol , combinatorial chemistry , organic chemistry , medicinal chemistry , mathematical analysis , mathematics

The selective synthesis of cis-3,4-disubstituted pyrrolidines and piperidines is achieved by a Pd-catalyzed C-H arylation with excellent regio- and stereoselectivity using an aminoquinoline auxiliary at C(3). The arylation conditions are silver free, use a low catalyst loading, and employ inexpensive K 2 CO 3 as a base. Directing group removal is accomplished under new, mild conditions to access amide-, acid-, ester-, and alcohol-containing fragments and building blocks. This C-H arylation protocol enabled a short and stereocontrolled formal synthesis of (-)-paroxetine.

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