Phase-Transfer-Catalyzed Asymmetric Annulations of Alkyl Dihalides with Oxindoles: Unified Access to Chiral Spirocarbocyclic Oxindoles

Gao, Min; Li, Yongyi; Li, Xuemin; Hu, Lin

doi:10.1021/acs.orglett.1c04174

Cited by 8 publications

(4 citation statements)

References 36 publications

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“…An alternative approach to spirocyclic carboxylic acid 197 was reported in 2022 by Hu and co-workers [ 100 ]. It involves the direct asymmetric spiroannulation of Boc-protected 7-azaindolin-2-one ( 213 ) with the doubly benzylic bis-bromide 212 .…”

Section: Ubrogepantmentioning

confidence: 99%

“…Oliceridine (Figure 20), a spirocyclic biased [101] agonist of µ-opioid receptors was developed by Trevena, Inc. and was approved in 2020 for the intravenous treatment of acute moderate-to-severe post-operative pain [102]. An alternative approach to spirocyclic carboxylic acid 197 was reported in 2022 by Hu and co-workers [100]. It involves the direct asymmetric spiroannulation of Boc-protected 7-azaindolin-2-one (213) with the doubly benzylic bis-bromide 212.…”

Section: Oliceridinementioning

confidence: 99%

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Synthetic Routes to Approved Drugs Containing a Spirocycle

et al. 2023

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The use of spirocycles in drug discovery and medicinal chemistry has been booming in the last two decades. This has clearly translated into the landscape of approved drugs. Among two dozen clinically used medicines containing a spirocycle, 50% have been approved in the 21st century. The present review focuses on the notable synthetic routes to such drugs invented in industry and academia, and is intended to serve as a useful reference source of synthetic as well as general drug information for researchers engaging in the design of new spirocyclic scaffolds for medicinal use or embarking upon analog syntheses inspired by the existing approved drugs.

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Section: Ubrogepantmentioning

confidence: 99%

Section: Oliceridinementioning

confidence: 99%

Synthetic Routes to Approved Drugs Containing a Spirocycle

et al. 2023

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“…Removal of the Boc group gave epimeric amine 202 which was subjected to crystallization induced diastereoselective transformation (CIDT) with p-toluic acid and 3,5-dichlorosalicylic aldehyde to give building block 203 which was converted to hydrochloride salt 198 (Scheme 52). An alternative approach to spirocyclic carboxylic acid 197 was reported in 2022 by Hu and coworkers [99]. It involves direct asymmetric spiroannulation of Boc-protected 7-azaindolin-2-one (213) with doubly benzylic bis-bromide 212.…”

Section: Ubrogepantmentioning

confidence: 99%

Synthetic Routes to Approved Drugs Containing a Spirocycle

Moshnenko¹,

Kazantsev²,

Chupakhin³

et al. 2023

Preprint

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The use of spirocycles in drug discovery and medicinal chemistry has been booming in the last two decades. This has clearly translated in the landscape of approved drugs. Among two dozen clinically used medicines containing a spirocycle, 50% have been approved in the 21st century. The present review focuses on the notable synthetic routes to such drugs invented in industry and academia and is intended to serve as a useful reference source of synthetic as well as general drug information for researchers engaging in the design of new spirocyclic scaffolds for medicinal use or embarking upon analog syntheses inspired by the existing approved drugs.

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“…C3-substituted oxindoles exist extensively in biologically active compounds, 2,9 and they are also appreciated as fundamental building blocks 10 and reaction intermediates 11 due to the wide range of synthetic opportunities. Accordingly, the synthesis and transformation of C3-substituted oxindoles as well as their derivatives receive intense research focus, especially in the total synthesis of complex molecules.…”

Section: Introductionmentioning

confidence: 99%