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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-212-00234
C-1 Building Blocks in Organic Synthesis 1

1.3.1 Stereoselective (Nucleophilic) Methylation of Ketones and Aldehydes

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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

Direct nucleophilic 1,2-methylations of aldehydes or ketones with polar methylmetal systems (e.g., methyllithium or Grignard reagents) are rarely (enantio)selective, due to fast background reactions. However, procedures with special chiral additives or even catalytic versions based on methylzinc or methyltitanium intermediates enable high and reliable selectivities with many substrates. Most modern are nickel and rhodium catalysts in cooperation with trimethylaluminum, providing catalytic and highly stereoselective methylations of aldehydes and ketones.

Schlüsselwörter

methylations - enantioselectivity - catalysis - aldehydes - ketones - methyllithium - methyl Grignard reagents - dimethylzinc - trimethylaluminum - methylnickel species - methylrhodium species - methylchromium species - methyltitanium species
 
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