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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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Enantioselective desymmetrizationof a meso-ditriflate.
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fig32: Enantioselective desymmetrizationof a meso-ditriflate.

Mentions: In a distinct desymmetrizationapproach, Willis and co-workersreported the asymmetric Suzuki–Miyaura cross-coupling of meso-ditriflate 102.132 The catalyst generated from Pd(OAc)2 and chiral biarylylphosphine L57 furnished monoarylated 103 bearing a stereodefinedquaternary center (Figure 32). Even though the yield of the transformation was moderate,good enantioselectivity was still accomplished. The remaining triflateon 103 was shown to serve as a versatile handle for furtherdiversification of the reaction products.


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)

Enantioselective desymmetrizationof a meso-ditriflate.
© Copyright Policy
Related In: Results  -  Collection

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

fig32: Enantioselective desymmetrizationof a meso-ditriflate.
Mentions: In a distinct desymmetrizationapproach, Willis and co-workersreported the asymmetric Suzuki–Miyaura cross-coupling of meso-ditriflate 102.132 The catalyst generated from Pd(OAc)2 and chiral biarylylphosphine L57 furnished monoarylated 103 bearing a stereodefinedquaternary center (Figure 32). Even though the yield of the transformation was moderate,good enantioselectivity was still accomplished. The remaining triflateon 103 was shown to serve as a versatile handle for furtherdiversification of the reaction products.

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.