First photosensitized enantiodifferentiating polar addition: anti-markovnikov methanol addition to 1,1-diphenylpropene

Inoue, Yoshihisa; Okano, Toshinori; Yamasaki, Noritsugu; Tai, Akira

doi:10.1039/c39930000718

Cited by 29 publications

(16 citation statements)

References 27 publications

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“…In some instances interesting cyclizations of the resulting radical were triggered after attack by alcohols at the @'+ Also the first enantioselective methanol addition under PET conditions was recently realized, [413] which required the enantiofacial-differentiating step to take place in a contact ion pair. [414] Further synthetic use of such @'+-Nu reactions was explored in intermolecular C-C bond formations starting from enamine['w.…”

Section: Reviewmentioning

confidence: 99%

Understanding Reactivity Patterns of Radical Cations

Schmittel

Burghart

1997

Angew. Chem. Int. Ed. Engl.

373

218

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cOver the last 15 years electron transfer activation has emerged as a valuable concept for accomplishing novel reactions and has €ound widespread application in the selective transformation of increasingly complex molecules. This review presents in a conceptualized manner the vast number of \ radical cation reactions obtained after chemical, electrochemical, and photoinduced one-electron oxidation. To familiarize the reader with the concepts of electron transfer a simple and straightforward classification of radical cation reactions has been devised to allow the presentation of a manifold . of reactions in a readily understandable manner. Whenever possible, thermochemical and kinetic data are provided.

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Section: Reviewmentioning

confidence: 99%

Understanding Reactivity Patterns of Radical Cations

Schmittel

Burghart

1997

Angew. Chem. Int. Ed. Engl.

373

218

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“…A first report on this reaction class from the Inoue group dates back to the year 1993. [30] Potential chiral catalysts for this reactions are modified cyclodextrins [31] or naphthalene carboxylates. [14,32] The addition of 2-propanol to 1,1-diphenylpropene (19) catalyzed by chiral diester 6 is shown in Scheme 4.…”

Section: Methodsmentioning

confidence: 99%

Enantioselective Catalysis of Photochemical Reactions

et al. 2015

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The nature of the excited state renders the development of chiral catalysts for enantioselective photochemical reactions a considerable challenge. The absorption of a 400 nm photon corresponds to an energy uptake of approximately 300 kJ mol(-1) . Given the large distance to the ground state, innovative concepts are required to open reaction pathways that selectively lead to a single enantiomer of the desired product. This Review outlines the two major concepts of homogenously catalyzed enantioselective processes. The first part deals with chiral photocatalysts, which intervene in the photochemical key step and induce an asymmetric induction in this step. In the second part, reactions are presented in which the photochemical excitation is mediated by an achiral photocatalyst and the transfer of chirality is ensured by a second chiral catalyst (dual catalysis).

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“…In 1993, Inoue's group reported the first photosensitized enantioselective anti-Markovnikov addition of methanol to 1,1-diphenylpropene (43a). 27 Using chiral naphthalenecarboxylates 45 as the photosensitizers, this reaction afforded optically active 1,1-diphenyl-2methoxypropane (44a), but in very low yields and enantioselectivities (Scheme 10, a and b). 28 Using supercritical carbon dioxide (scCO 2 ) as the solvent slightly improved the yield and enantioselectivity, but still far from being practical in synthesis (Scheme 10, c).…”

Section: Intermolecular Additionsmentioning

confidence: 99%

Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation

Xie

Li²

2020

Synthesis

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Many chiral ethers have important physiological activities. Although many asymmetric hydroalkoxylations of olefins with alcohols or phenols have been developed to make chiral ethers, challenges still remain in achieving high reactivity and selectivity over an ever-increasing diversity of alkenes and alcohols. In this review, recent developments on catalytic asymmetric alkene hydroalkoxylations are summarized based on the substitution patterns of alkenes.1 Introduction2 Asymmetric Hydroalkoxylation of Non-Activated Alkenes2.1 Intramolecular Additions2.2 Intermolecular Additions3 Asymmetric Hydroalkoxylation of Enol Ethers3.1 Intramolecular Additions3.2 Intermolecular Additions4 Asymmetric Hydroalkoxylation of α,β-Unsaturated Carbonyl Compounds4.1 α,β-Unsaturated Ketones and Aldehydes as Substrates4.2 α,β-Unsaturated Esters, Amides and Carboxylic Acids as Substrates5 Asymmetric Hydroalkoxylation of Allenes5.1 Intramolecular Additions5.2 Intermolecular Additions6 Conclusion

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First photosensitized enantiodifferentiating polar addition: anti-markovnikov methanol addition to 1,1-diphenylpropene

Cited by 29 publications

References 27 publications

Understanding Reactivity Patterns of Radical Cations

Understanding Reactivity Patterns of Radical Cations

Enantioselective Catalysis of Photochemical Reactions

Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation

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First photosensitized enantiodifferentiating polar addition: anti-markovnikov methanol addition to 1,1-diphenylpropene

Cited by 29 publications

References 27 publications

Understanding Reactivity Patterns of Radical Cations

Understanding Reactivity Patterns of Radical Cations

Enantioselective Catalysis of Photochemical Reactions

Asymmetric Synthesis of Ethers by Catalytic Alkene Hydro­alkoxy­lation

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Product

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Asymmetric Synthesis of Ethers by Catalytic Alkene Hydroalkoxylation