Asymmetric Synthesis of Quinoline-Naphthalene Atropisomers by Central-to-Axial Chirality Conversion

Wang, Shaojie; Wang, Zhe; Tang, Yue; Chen, Jie; Zhou, Ling

doi:10.1021/acs.orglett.0c03285

Cited by 47 publications

(23 citation statements)

References 50 publications

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“…SI, page S65) [18,19] . Namely, we found that the C(1′)−C(4) bond of dihydronaphthalenes 8 is inverted in this chirality exchange, and this result is consistent with Hayashi's report [6b] …”

Section: Resultssupporting

confidence: 92%

From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange

et al. 2021

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Transformations of enantioenriched donor‐acceptor (D−A) cyclopropylcarbinols to enantioenriched 1‐arylnaphthalenes that bear an ortho‐substituent on a benzene ring provided a successful chirality‐exchange method with a high level of stereoinduction. A central chirality‐transfer step, i. e., a Lewis‐acid‐mediated ring‐opening cyclization of enantioenriched D‐A cyclopropylcarbinols (97 to >99 % ee), afforded 1‐aryl‐1,2‐dihydronaphthalenes with an ortho‐substituent (Me, Br, OMe, OBn, or OiPr) on the benzene ring with high enantioselectivity (97 to >99 % ee). The central‐to‐axial chirality‐exchange step, i. e., the dehydrogenation of the obtained enantioenriched 1‐aryl‐1,2‐dihydronaphthalenes using DDQ, furnished the axially chiral 1‐arylnaphthalenes with high enantioselectivity (90 to >99 % ee). Importantly, we developed a highly enantioselective synthesis of a 1‐arylnaphthalene with an ortho‐alkoxy group on the benzene ring. Moreover, we improved the chirality exchange to furnish a 1‐arylnaphthalene with an ortho‐alkoxy‐substituted benzene ring in high yield with high ee.

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Section: Resultssupporting

confidence: 92%

From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange

et al. 2021

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“…The route starts with the enantioselective multicomponent PR catalyzed by chiral Brønsted acid 123 to afford THQs 124 with good yields (62-80 %) and enantioselectivities (91-98 % ee), followed by an oxidation with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) that leads to the conversion from central to axial chirality, thus forming the atropisomers 125 (Scheme 26). [84] Scheme 22. Three-step synthetic route for the formation of polycyclic THQ derivatives.…”

Section: E Richmond Et Al Investigated a Multicatalytic Version Of Prmentioning

confidence: 99%

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

et al. 2022

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The enantioselective Povarov reaction is one of the most powerful synthetic strategy to synthesize chiral, highly functionalized 1,2,3,4-tetrahydroquinolines. The present Minireview aims to collect the most significant successful examples of highly efficient enantioselective catalytic protocols for this reaction, since 2014. A comprehensive discussion of different catalytic strategies employed in recent years to realize the enantioselec-tive Povarov reaction is provided; the use of chiral phosphoric acids, thio(urea) and proline derivatives, as well as transition metal complexes will be presented. Additionally, this Minireview critically discusses the intriguing and yet obscure mechanistic pathways of this well-known reaction, the controversial dispute between a concerted or a polar two-step process.

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“…Finally, the utility of this strategy was proven by its scalability and the possibility to exploit the functionalization pattern of the products to obtain more complex structures. 45 3.1.4. Indoles as dienophiles.…”

Section: Organic and Biomolecular Chemistry Reviewmentioning

confidence: 99%

Enantioselective catalytic Povarov reactions

2022

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Asymmetric Synthesis of Quinoline-Naphthalene Atropisomers by Central-to-Axial Chirality Conversion

Cited by 47 publications

References 50 publications

From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange

From Enantioenriched Donor‐Acceptor Cyclopropylcarbinols to Axially Chiral Arylnaphthalenes through Aryldihydronaphthalenes: Central‐to‐Axial Chirality Exchange

Enantioselective Povarov Reactions: An Update of a Powerful Catalytic Synthetic Methodology

Enantioselective catalytic Povarov reactions

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