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Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Cherney AH, Kadunce NT, Reisman SE - Chem. Rev. (2015)

View Article: PubMed Central - PubMed

Affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

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reagents in asymmetric alkyl cross-coupling reactions, with Hayashi, a single example of an asymmetric cross-coupling between sec-alkyl organic halides and organosilicon reagents has been reported stereoconvergent cross-coupling reactions between sec-alkyl electrophiles and either C(sp)- or C(sp)-hybridized organometallic reagents, Sestelo, Sarandeses, (Scheme 9a)... This result and π-allylmetal complex... Unselective reductive selectivity for the (Z)-alkene in most cases; MeMgBr resulted in decreased regioselectivity... increasing the C1–C1′ separation and disfavoring 1,1′ reductive elimination... use in asymmetric allylic alkylation reactions: any successful transformations the allenylmetal and its isomeric propargylmetal species prior to reductive elimination... the analogous asymmetric cross-coupling reactions of tert-alkyl partners represent a largely undeveloped area of great synthetic

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Cu-catalyzed propargylic arylation and vinylation withorganoboronates.
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fig103: Cu-catalyzed propargylic arylation and vinylation withorganoboronates.

Mentions: A year later, Sawamura and Lalic independently reported theCu-catalyzedstereospecific coupling of propargylic phosphates 528 with either aryl- or vinylboronate reagents (Figure 103a).421 The Sawamura coupling employed either CuCl or CuCl2 asthe catalyst, under conditions similar to those utilized in the previouslyreported enantiospecific arylation of allylic phosphates.332 On the other hand, Lalic and co-workers identifieda Cu–NHC catalyst that provided the enantioenriched allenein good yield and with excellent point-to-axial chirality transfer(Figure 103b).420 Under Lalic’s conditions, both aryl-and alkylboron reagents were found to react with high stereochemicalfidelity.


Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Cherney AH, Kadunce NT, Reisman SE - Chem. Rev. (2015)

Cu-catalyzed propargylic arylation and vinylation withorganoboronates.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4566132&req=5

fig103: Cu-catalyzed propargylic arylation and vinylation withorganoboronates.
Mentions: A year later, Sawamura and Lalic independently reported theCu-catalyzedstereospecific coupling of propargylic phosphates 528 with either aryl- or vinylboronate reagents (Figure 103a).421 The Sawamura coupling employed either CuCl or CuCl2 asthe catalyst, under conditions similar to those utilized in the previouslyreported enantiospecific arylation of allylic phosphates.332 On the other hand, Lalic and co-workers identifieda Cu–NHC catalyst that provided the enantioenriched allenein good yield and with excellent point-to-axial chirality transfer(Figure 103b).420 Under Lalic’s conditions, both aryl-and alkylboron reagents were found to react with high stereochemicalfidelity.

View Article: PubMed Central - PubMed

Affiliation: The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.

AUTOMATICALLY GENERATED EXCERPT
Please rate it.

reagents in asymmetric alkyl cross-coupling reactions, with Hayashi, a single example of an asymmetric cross-coupling between sec-alkyl organic halides and organosilicon reagents has been reported stereoconvergent cross-coupling reactions between sec-alkyl electrophiles and either C(sp)- or C(sp)-hybridized organometallic reagents, Sestelo, Sarandeses, (Scheme 9a)... This result and π-allylmetal complex... Unselective reductive selectivity for the (Z)-alkene in most cases; MeMgBr resulted in decreased regioselectivity... increasing the C1–C1′ separation and disfavoring 1,1′ reductive elimination... use in asymmetric allylic alkylation reactions: any successful transformations the allenylmetal and its isomeric propargylmetal species prior to reductive elimination... the analogous asymmetric cross-coupling reactions of tert-alkyl partners represent a largely undeveloped area of great synthetic

No MeSH data available.