Intramolecular N-Me and N-H aminoetherification for the synthesis of <i>N</i>-unprotected 3-amino-O-heterocycles.

Paudyal, Mahesh P; Wang, Mingliang; Siitonen, Juha H; Hu, Yimin; Yousufuddin, Muhammed; Shen, Hong C; Falck, John R; Kürti, László

Intramolecular N-Me and N-H aminoetherification for the synthesis of N-unprotected 3-amino-O-heterocycles.

Paudyal, Mahesh P; Wang, Mingliang; Siitonen, Juha H; Hu, Yimin; Yousufuddin, Muhammed; Shen, Hong C; Falck, John R; Kürti, László.

Afiliação

Paudyal MP; Division of Chemistry, Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu.
Wang M; Department of Natural Products Chemistry, Fudan University, 826 Zhangheng Road, Shanghai 201203, P. R. China.
Siitonen JH; Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77030, USA. lk18@rice.edu.
Hu Y; Roche Pharma Research & Early Development, Roche Innovation Center Shanghai, Roche R&D Center (China) Ltd, Building 5, No. 371, Lishizhen Road, Shanghai 201203, P. R. China. hong.shen.hs1@roche.com.
Yousufuddin M; Life and Health Sciences Department, The University of North Texas at Dallas, 7400 University Hills Boulevard, Dallas, TX 75241, USA.
Shen HC; Roche Pharma Research & Early Development, Roche Innovation Center Shanghai, Roche R&D Center (China) Ltd, Building 5, No. 371, Lishizhen Road, Shanghai 201203, P. R. China. hong.shen.hs1@roche.com.
Falck JR; Division of Chemistry, Departments of Biochemistry and Pharmacology, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA. j.falck@utsouthwestern.edu.
Kürti L; Department of Chemistry, Rice University, 6500 Main Street, Houston, Texas 77030, USA. lk18@rice.edu.

Org Biomol Chem ; 19(3): 557-560, 2021 01 28.

Article em En | MEDLINE | ID: mdl-33399609

ABSTRACT

ABSTRACT

A mild Rh-catalyzed method for synthesis of cyclic unprotected N-Me and N-H 2,3-aminoethers using an olefin aziridination-aziridine ring-opening domino reaction has been developed. The method is readily applicable to the stereocontrolled synthesis of a variety of 2,3-disubstituted aminoether O-heterocyclic scaffolds, including tetrahydrofurans, tetrahydropyrans and chromanes.

Assuntos

Éteres/química; Compostos Heterocíclicos/química; Compostos Heterocíclicos/síntese química; Nitrogênio/química; Técnicas de Química Sintética; Hidrogênio/química; Estereoisomerismo

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Éteres / Compostos Heterocíclicos / Nitrogênio Idioma: En Ano de publicação: 2021 Tipo de documento: Article

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