Construction of β‐Phenylalanine Derivatives through Pd‐Catalyzed, C(sp2)−H (ortho) Functionalization

Author:

Narang Urja1,Singh Prabhakar1,Arulananda Babu Srinivasarao1

Affiliation:

1. Department of Chemical Sciences Indian Institute of Science Education and Research (IISER) Mohali Knowledge City, Sector 81 SAS Nagar, Mohali, Manauli P.O. Punjab 140306 India

Abstract

AbstractThis paper describes the Pd(II)‐catalyzed, picolinamide‐directing‐group‐aided C(sp2)−H (ortho) functionalization of racemic and enantiopure β‐phenylalanines and 3‐amino‐3‐phenylpropanols (1,3‐amino alcohols). The C(sp2)−H (ortho) functionalizations including arylation, bromination, iodination, and alkoxylation were attempted. The C(sp2)−H (ortho) arylation reactions gave biaryl or terphenyl‐type β‐phenylalanine scaffolds, halogenation and methoxylation reactions gave ortho C−H halogenated or methoxylated β‐phenylalanines. Additionally, the C−H arylation of an ortho‐methyl substituted β‐phenylalanine containing both C(sp2)−H and remote C(sp3)−H bonds was investigated. β‐Phenylalanine is an arylated β‐amino acid motif present in various natural products, bioactive molecules, and β‐peptides and it is a precursor to medicinally active compounds. Accordingly, this work contributes to the expansion of the library of unnatural β‐phenylalanine (β‐amino acid) derivatives through site‐selective C−H functionalization.

Funder

Indian Institute of Science Education and Research Mohali

Publisher

Wiley

Subject

Organic Chemistry,Physical and Theoretical Chemistry

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