Assembly of indoline-2-carboxylate-embodied dipeptides via Pd-catalyzed C(sp2)-H bond direct functionalization

Yu-Peng He; Chao Zhang; Mengyang Fan; Zhijie Wu; Dawei Ma

doi:10.1021/ol503514t

Assembly of indoline-2-carboxylate-embodied dipeptides via Pd-catalyzed C(sp2)-H bond direct functionalization

Org Lett. 2015 Feb 6;17(3):496-9. doi: 10.1021/ol503514t. Epub 2015 Jan 20.

Authors

Yu-Peng He¹, Chao Zhang, Mengyang Fan, Zhijie Wu, Dawei Ma

Affiliation

¹ College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University , Dandong Lu West 1, Fushun 113001, China.

PMID: 25602435
DOI: 10.1021/ol503514t

Abstract

Intramolecular dehydrogenative cyclization of 2-methoxyiminoacyl-protected phenylalanine derivatives proceeded at 110 °C under catalysis of Pd(OAc)2 in the presence of 1-fluoro-2,4,6-trimethylpyridinium tetrafluoroborate to afford substituted indoline-2-carboxylates that were converted into indoline-2-carboxylate-embodied dipeptides via Raney Ni-catalyzed hydrogenation.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / chemical synthesis*
Carboxylic Acids / chemistry
Catalysis
Cyclization
Dipeptides / chemical synthesis*
Dipeptides / chemistry
Hydrogenation
Indoles / chemical synthesis*
Indoles / chemistry
Molecular Structure
Palladium / chemistry*

Substances

Carboxylic Acids
Dipeptides
Indoles
indoline-2-carboxylate
Palladium
indoline