Synthesis of a TNF inhibitor, flurbiprofen and an i-Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents-Reference-Cited by-同舟云学术

Synthesis of a TNF inhibitor, flurbiprofen and an i-Pr analogue in enantioenriched forms by copper-catalyzed propargylic substitution with Grignard reagents

Published:2021 Issue:45 Volume:19 Page:9906-9909
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Takashima Yuji¹,Isogawa Yukari¹,Tsuboi Atsuki²,Ogawa Narihito²^ORCID,Kobayashi Yuichi¹³^ORCID

Affiliation:

1. Department of Biomolecular Engineering, Tokyo Institute of Technology, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan

2. Department of Applied Chemistry, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan

3. Organization for the Strategic Coordination of Research and Intellectual Properties, Meiji University, 1-1-1, Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan

Abstract

The Cu-catalyzed substitution reaction of propargylic phosphates with ArMgBr was demonstrated to be suited for the synthesis of a TNF inhibitor, flurbiprofen and an i-Pr analogue.

Funder

Japan Society for the Promotion of Science

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2021/OB/D1OB01944A

Reference47 articles.

1. Picolinoxy Group, a New Leaving Group for anti SN2′ Selective Allylic Substitution with Aryl Anions Based on Grignard Reagents

2. New General Method for Regio- and Stereoselective Allylic Substitution with Aryl and Alkenyl Coppers Derived from Grignard Reagents

3. Formation of Chiral C(sp3)−C(sp) Bond by Allylic Substitution of Secondary Allylic Picolinates and Alkynyl Copper Reagents