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van Leeuwen, P. W. N. M.: 2014 Science of Synthesis, 2013/7: C-1 Building Blocks in Organic Synthesis 1 DOI: 10.1055/sos-SD-212-00203
C-1 Building Blocks in Organic Synthesis 1

1.1.10 Stereoselective Conjugate Addition of Methyl and Cyanide

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Buch

Herausgeber: van Leeuwen, P. W. N. M.

Autoren: Ballini, R.; Belderrain, T. R.; Bronger, R. P. J.; Clarke, M. L.; Claver, C.; de Vries, J. G.; Feng, X. M.; Fleischer, I.; Fuentes, J. A.; Godard, C.; Goldfuss, B.; Iwasawa, N.; Kamer, P. C. J.; Lin, L. L.; Liu, X. H.; Mejía, E.; Monflier, E.; Mortreux, A.; Nicasio, M. C.; Perandones, B. F.; Petrini, M.; Sauthier, M.; Takaya, J.; Tauchert, M. E.; Tilloy, S.; Vogt, D.

Titel: C-1 Building Blocks in Organic Synthesis 1

Untertitel: Additions to Alkenes, Alkynes, and Carbonyl Compounds

Print ISBN: 9783131707611; Online ISBN: 9783132064416; Buch-DOI: 10.1055/b-003-125818

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Fachgebiete: C1-bildende Blöcke in der organischen Synthese

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Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

Typ: Mehrbändiges Werk

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Abstract

Conjugate additions of methyl and cyanide nucleophiles to Michael acceptors are powerful methods for stereoselective homologation. New ligands and a variety of copper sources today enable highly enantioselective nucleophilic 1,4-methylations. Besides Grignard reagents, methylzinc reagents and trimethylaluminum are well established as nucleophilic methyl sources. Enantioselective cyanations of alkenes, aldehydes, or imines can be accomplished with metal catalysts (e.g., based on nickel, aluminum, or titanium) or organocatalysts, mostly employing silyl cyanides or acetone cyanohydrin as the cyanide source.

Schlüsselwörter

copper catalysts - methyl Grignard reagents - methylaluminum reagents - cyanide - asymmetric catalysis - asymmetric synthesis - conjugate addition - CC bonds - carbonheteroatom bonds - Michael acceptors - nucleophilic addition
 
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