Late-Stage Chemo- and Enantioselective Oxidation of Indoles to C3-Monosubstituted Oxindoles

Li, Song; Liu, Xigong; Tung, Chen-Ho; Liu, Lei

doi:10.1021/jacs.3c11742

Cited by 5 publications

(2 citation statements)

References 75 publications

(39 reference statements)

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“…The combination of salen and group 4 transition-metals have enabled various exceptional asymmetric oxidations, ,− where structural characterizations of catalysts facilitated the mechanism elucidations. Since the Hf-salen complex was able to achieve outstanding reactivity in epoxidation, its catalysis model was worth studying.…”

Section: Results and Discussionmentioning

confidence: 99%

Hafnium(IV)-Salen-Catalyzed Highly Reactive and Enantioselective Epoxidation Directed by Amides

Yao,

2024

ACS Catal.

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Substrate-directed enantioselective olefin epoxidation was limited to a few types of directing groups and relatively low catalyst activities. Herein, an expeditious asymmetric epoxidation protocol is reported for allylic amides and sulfonamides using a hafnium-BINAM-salen catalyst with high enantioselectivity and turnover frequency. Aryl carboxamides of allylic amines with a trisubstituted olefin motif were suitable substrates. Sequential intramolecular ringopening in a one-pot reactor furnished highly enantiopure oxazoline alcohols. Crystallographic studies suggested the catalyst possessed a mononuclear cis-α configuration. Computational studies of the transition state indicated that this conversion underwent a substrate-directed pathway.

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Section: Results and Discussionmentioning

confidence: 99%

Hafnium(IV)-Salen-Catalyzed Highly Reactive and Enantioselective Epoxidation Directed by Amides

Yao,

2024

ACS Catal.

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“…In this section we briefly discuss the magnesium catalytic method for the asymmetric synthesis of indole- or oxindole-related structures (Scheme 19). 54 Pyrroloindolines bearing a C3 quaternary stereocenter are common and important building blocks and serve as a typical subclass of indole alkaloids. In 2015, our group achieved a direct synthetic strategy for rapid construction of pyrroloindolines by using C3-substituted indole and meso -aziridine as easily accessed feedstocks.…”

Section: The Enantioselective Synthesis Of Indole- or Oxindole-relate...mentioning

confidence: 99%