Cu-Catalyzed Enantioselective Atropisomer Synthesis via Thiolative Ring Opening of Five-Membered Cyclic Diaryliodoniums

Hou, Mengqing; Deng, Ruixian; Gu, Zhenhua

doi:10.1021/acs.orglett.8b02477

Cited by 59 publications

(21 citation statements)

References 87 publications

(22 reference statements)

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“…Potassium thiolates as sulfur nucleophiles gave atropisomerically enriched 2′-iodo-[1,1′-biphenyl]-2-yl thioates 115 using Cu(CH 3 CN) 4 PF 6 /(Ph)-bis(oxazoline) system (Scheme 41b). 139 Counteranion PF 6 − induced better enantioselectivity outcome than OTf − due to weak coordination capability of the latter. Aliphatic thioates (115a), benzothioates (115b), the bulkier analogue (115c) as well as naphthalene-2-carbothioate (115d) were among amenable nucleophiles.…”

Section: Atroposelective Functionalization Of Prochiral/racemic Biarylsmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

et al. 2021

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Atropisomerism is a stereochemical behavior portrayed by three-dimensional molecules that bear rotationally restricted σ bond. Akin to the well-represented point-chiral molecules, atropisomerically chiral compounds are finding increasing utilities in many disciplines where molecular asymmetry is influential. This provides steady demand on atroposelective synthesis, where numerous synthetic pursuits have been rewarded with conceptually novel and streamlined methods while expanding the structural diversity of atropisomers. This review summarizes key achievements in stereoselective preparation of biaryl, heterobiaryl, and nonbiaryl atropisomers documented between 2015 and 2020. Emphasis is placed on the synthetic strategies for each structural class, while examples are cited to illustrate the potential applications of the accessed atropochiral targets.

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Section: Atroposelective Functionalization Of Prochiral/racemic Biarylsmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

et al. 2021

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“…22 Aiming to introduce new functionalities into this system, the same group reported a Cu-catalysed asymmetric thiolative ring opening reaction for the synthesis of atropisomeric 2-thio-2 0 -iodo-1,1 0 -biphenyl derivatives. 23 In this case, the use of potassium thiocarboxylates as nucleophiles and Cu(CH 3 CN) 4 PF 6 /PhBOX as the optimal catalytic system delivered the desired thioesters satisfactorily in terms of reactivity and enantioselectivity (Scheme 10D). These diaryliodoniums were also used in the synthesis of lactone-bridged biaryl atropisomers.…”

Section: Desymmetrization Of Biaryls Via Ring-opening Reactions ‡mentioning

confidence: 97%

Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies

et al. 2021

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“…While most substrates were tolerated, bulky aryl thioates 609 appeared to reduce the enantioselectivity to as low as 86% ee . 228 …”

Section: Bis(oxazoline) Ligandsmentioning

confidence: 99%

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

et al. 2021

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The chiral oxazoline motif is present in many ligands that have been extensively applied in a series of important metal-catalyzed enantioselective reactions. This Review aims to provide a comprehensive overview of the most significant applications of oxazoline-containing ligands reported in the literature starting from 2009 until the end of 2018. The ligands are classified not by the reaction to which their metal complexes have been applied but by the nature of the denticity, chirality, and donor atoms involved. As a result, the continued development of ligand architectural design from mono(oxazolines), to bis(oxazolines), to tris(oxazolines) and tetra(oxazolines) and variations thereof can be more easily monitored by the reader. In addition, the key transition states of selected asymmetric transformations will be given to illustrate the features that give rise to high levels of asymmetric induction. As a further aid to the reader, we summarize the majority of schemes with representative examples that highlight the variation in % yields and % ee s for carefully selected substrates. This Review should be of particular interest to the experts in the field but also serve as a useful starting point to new researchers in this area. It is hoped that this Review will stimulate both the development/design of new ligands and their applications in novel metal-catalyzed asymmetric transformations.

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Cu-Catalyzed Enantioselective Atropisomer Synthesis via Thiolative Ring Opening of Five-Membered Cyclic Diaryliodoniums

Cited by 59 publications

References 87 publications

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Atroposelective transformation of axially chiral (hetero)biaryls. From desymmetrization to modern resolution strategies

Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis

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