Substrate-Directed Catalytic Selective Chemical Reactions

The Journal of Organic Chemistry
Takahiro Sawano, Hisashi Yamamoto

Abstract

The development of highly efficient reactions at only the desired position is one of the most important subjects in organic chemistry. Most of the reactions in current organic chemistry are reagent- or catalyst-controlled reactions, and the regio- and stereoselectivity of the reactions are determined by the inherent nature of the reagent or catalyst. In sharp contrast, substrate-directed reaction determines the selectivity of the reactions by the functional group on the substrate and can strictly distinguish sterically and electronically similar multiple reaction sites in the substrate. In this Perspective, three topics of substrate-directed reaction are mainly reviewed: (1) directing group-assisted epoxidation of alkenes, (2) ring-opening reactions of epoxides by various nucleophiles, and (3) catalytic peptide synthesis. Our newly developed synthetic methods with new ligands including hydroxamic acid derived ligands realized not only highly efficient reactions but also pinpointed reactions at the expected position, demonstrating the substrate-directed reaction as a powerful method to achieve the desired regio- and stereoselective functionalization of molecules from different viewpoints of reagent- or catalyst-controlled reacti...Continue Reading

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Citations

Oct 3, 2020·Chemical Communications : Chem Comm·Naoyuki ShimadaKazuishi Makino
Apr 3, 2020·Chemistry : a European Journal·Robert R A FreundHans-Dieter Arndt
Feb 13, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Lei ZhangShaodan Li
Jun 25, 2020·Journal of the American Chemical Society·Elizabeth A StoneScott J Miller
Jun 15, 2021·Chemical Communications : Chem Comm·Wataru MuramatsuHisashi Yamamoto
Oct 21, 2020·The Journal of Organic Chemistry·Aran K Hubbell, Geoffrey W Coates
May 22, 2020·Journal of the American Chemical Society·Guangrong MengJin-Quan Yu
Aug 28, 2018·Organic Letters·Grace WangMark S Taylor
Aug 21, 2021·Journal of the American Chemical Society·Taeho KangKeary M Engle
Dec 27, 2019·The Journal of Organic Chemistry·Yoshiyuki TakahashiMotoi Kawatsura
Nov 16, 2019·Journal of the American Chemical Society·Wataru Muramatsu, Hisashi Yamamoto

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