Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters

Iorio, Nicola Di; Soprani, Lorenzo; Crotti, Simone; Marotta, Emanuela; Mazzanti, Andrea; Righi, Paolo; Bencivenni, Giorgio

doi:10.1055/s-0036-1588408

Cited by 24 publications

(6 citation statements)

References 4 publications

(5 reference statements)

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“…256 The enantionenriched adduct with N-(tert-butoxycarbonyl)-3-phenyloxindole (390a) was produced with the use of squaramide cinchonidine organocatalyst Q19 (Scheme 128, conditions B). 257 Feng variously employed chiral N,N′-dioxide 392-Sc(OTf) 3 complex to engage unprotected 3-substituted-2-oxindoles 391 as nucleophiles (Scheme 129). 258 In the proposed stereodetermining transition state, oxygen atoms of L-RaPr 3 form tetradentate coordination with Sc III in six-membered chelating ring while carbonyl oxygen of oxindole enolates and maleimide occupy the remaining coordination sites.…”

Section: Heterobiaryl Atropisomersmentioning

confidence: 99%

“…This desymmetrization chemistry was further enriched by Michael addition of carbon nucleophiles encompassing α-acetylcyclopentanone ( 387a ), 2-cyano-2-phenylacetate ( 388a ), and α-acylbutyrolactone ( 389a ), promoted by (DHQD) 2 PYR catalyst Q18 (Scheme , conditions A) . The enantionenriched adduct with N -( tert -butoxycarbonyl)-3-phenyloxindole ( 390a ) was produced with the use of squaramide cinchonidine organocatalyst Q19 (Scheme , conditions B) …”

Section: Nonbiaryl Atropisomersmentioning

confidence: 99%

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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: Heterobiaryl Atropisomersmentioning

confidence: 99%

Section: Nonbiaryl Atropisomersmentioning

confidence: 99%

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

et al. 2021

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“…[32] Furthermore, this group extended the desymmetrizative Michael addition of N-aryl maleimides 23 to other carbon nucleophiles 47 and 49, which offered succinimides 48 and 50 bearing contiguous stereogenic centers and one CÀ N axis with excellent diastereo-and enantioselectivities (Scheme 10c-d). [33,34] In 2018, Tan and co-workers devised an asymmetric threecomponent ene reaction involving 4-aryl-1,2,4-triazole-3,5diones 51 (N-aryl maleimide analogs) to synthesize spirooxindole-urazoles 54 bearing both a chiral CÀ N axis and carbon stereocenters (Scheme 10e). [35] Recently, Wang, Lin, and co-workers developed an organocatalytic desymmetrizative (3 + 2) annulation of MBH carbonates 55 with N-aryl maleimides 23 to give nonbiaryl CÀ N atropisomers 56 with C-stereogenic centers in good results (Scheme 10f).…”

Section: Desymmetrization Of N-aryl Maleimides and Their Analogsmentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Zhang,

Li,

Liu

et al. 2023

Angew Chem Int Ed

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With the rapid development of asymmetric catalysis, the demand for the enantioselective synthesis of complex and diverse molecules with different chiral elements is increasing. Owing to the unique features of atropisomerism, the catalytic asymmetric synthesis of atropisomers has attracted a considerable interest from the chemical science community. In particular, introducing additional chiral elements, such as carbon center chirality, heteroatomic chirality, planar chirality, and helical chirality, into atropisomers provides an opportunity to incorporate new properties into axially chiral compounds, thus expanding the potential applications of atropisomers. Thus, it is important to perform catalytic asymmetric transformations to synthesize atropisomers bearing multiple chiral elements. In spite of challenges in such transformations, in recent years, chemists have devised powerful strategies under asymmetric organocatalysis or metal catalysis, synthesizing a wide range of enantioenriched atropisomers bearing multiple chiral elements. Therefore, the catalytic asymmetric synthesis of atropisomers bearing multiple chiral elements has become an emerging field. This minireview summarizes the rapid progress in this field and indicates challenges, thereby promoting this field to a new horizon.

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“…The chiral amine catalyst derived from cinchona alkaloids is first condensed with the conjugated diene, and the selective synthesis of a single enantiomer is achieved via H-bonding and steric hindrance. They also carried out a significant amount of research on desymmetrization with this type of catalyst, which is only listed for readers to consult as it is not relevant to the topic of this review [78,79].…”

Section: Scheme 23 Cinchona Alkaloidsmentioning

confidence: 99%

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

et al. 2023

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Atropisomeric molecules are present in many natural products, biologically active compounds, chiral ligands and catalysts. Many elegant methodologies have been developed to access axially chiral molecules. Among them, organocatalytic cycloaddition and cyclization have attracted much attention because they have been widely used in the asymmetric synthesis of biaryl/heterobiaryls atropisomers via construction of carbo- and hetero-cycles. This strategy has undoubtedly become and will continue to be a hot topic in the field of asymmetric synthesis and catalysis. This review aims to highlight the recent advancements in this field of atropisomer synthesis by using different organocatalysts in cycloaddition and cyclization strategies. The construction of each atropisomer, its possible mechanism, the role of catalysts, and its potential applications are illustrated.

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Michael Addition of Oxindoles to N-(2-tert-Butylphenyl)maleimides: Efficient Desymmetrization for the Synthesis of Atropisomeric Succinimides with Quaternary and Tertiary Stereocenters

Cited by 24 publications

References 4 publications

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Recent Advances in Catalytic Asymmetric Construction of Atropisomers

Catalytic Asymmetric Synthesis of Atropisomers Bearing Multiple Chiral Elements: An Emerging Field

Asymmetric Synthesis of Axially Chiral Molecules via Organocatalytic Cycloaddition and Cyclization Reactions

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