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

Autor:	Kang G; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Xiao LJ; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Hesp KD; Treeline Biosciences, 500 Arsenal St, second Floor, Watertown, Massachusetts 02472, United States., Huh CW; Medicine Design, Pfizer Inc., Groton, Connecticut 06340, United States., Lian Y; Medicine Design, Pfizer Inc., Groton, Connecticut 06340, United States., Richardson P; Medicine Design, Pfizer Inc., San Diego, California 92121, United States., Schmitt DC; Medicine Design, Pfizer Inc., Groton, Connecticut 06340, United States., Hong K; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States., Yu JQ; Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Jazyk:	angličtina
Zdroj:	Organic letters [Org Lett] 2024 Apr 12; Vol. 26 (14), pp. 2729-2732. Date of Electronic Publication: 2023 Jun 09.
DOI:	10.1021/acs.orglett.3c01439
Abstrakt:	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 and provided the corresponding products in moderate to good yields. The subsequent α-alkylation or arylation of the isolated arylated products proceeded with high diastereoselectivity to afford value-added disubstituted aminotetrahydropyrans.
Databáze:	MEDLINE
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