Distal γ‐C(sp 3 )−H Olefination of Ketone Derivatives and Free Carboxylic Acids | Zendy

Park Han Seul | Zendy; Fan Zhoulong | Zendy; Zhu RuYi | Zendy; Yu JinQuan | Zendy

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Distal γ‐C(sp 3 )−H Olefination of Ketone Derivatives and Free Carboxylic Acids

Author(s) -

Park Han Seul,

Fan Zhoulong,

Zhu RuYi,

Yu JinQuan

Publication year - 2020

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.202003271

Subject(s) - ketone , chemistry , carboxylic acid , benzoic acid , alkyl , ligand (biochemistry) , stereochemistry , organic chemistry , medicinal chemistry , biochemistry , receptor

Reported herein is the distal γ‐C(sp 3 )−H olefination of ketone derivatives and free carboxylic acids. Fine tuning of a previously reported imino‐acid directing group and using the ligand combination of a mono‐N‐protected amino acid (MPAA) and an electron‐deficient 2‐pyridone were critical for the γ‐C(sp 3 )−H olefination of ketone substrates. In addition, MPAAs enabled the γ‐C(sp 3 )−H olefination of free carboxylic acids to form diverse six‐membered lactones. Besides alkyl carboxylic acids, benzylic C(sp 3 )−H bonds also could be functionalized to form 3,4‐dihydroisocoumarin structures in a single step from 2‐methyl benzoic acid derivatives. The utility of these protocols was demonstrated in large scale reactions and diversification of the γ‐C(sp 3 )−H olefinated products.

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