Synthesis of Highly Substituted Aminotetrahydropyrans Enabled by Stereospecific Multivector C-H Functionalization.

Guowei Kang¹, Li-Jun Xiao¹, Kevin D Hesp², Chan Woo Huh³, Yajing Lian³, Paul Richardson⁴, Daniel C Schmitt³, Kai Hong¹, Jin-Quan Yu¹

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

²Treeline Biosciences, 500 Arsenal St, second Floor, Watertown, Massachusetts 02472, United States.

³Medicine Design, Pfizer Inc., Groton, Connecticut 06340, United States.

⁴Medicine Design, Pfizer Inc., San Diego, California 92121, United States.

PubMed PMC DOI PDF

Abstract

Highly substituted aminotetrahydropyrans were synthesized via sequential C-H functionalizations. The process was initiated with a Pd(II)-catalyzed stereoselective γ-methylene C-H arylation of aminotetrahydropyran, followed by α-alkylation or arylation of the corresponding primary amine. The initial γ-C-H (hetero)arylation was compatible with a range of aryl iodides containing various substituents…

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