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Banert, K. et al.: 2015 Science of Synthesis, 2014/4: Knowledge Updates 2014/4 DOI: 10.1055/sos-SD-101-00827
Knowledge Updates 2014/4

27.1.7 Sulfur Ylides (Update 2014)

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Book

Editors: Banert, K.; Hall, D. G.; Joule, J. A.; Moloney, M. G.; Reissig, H.-U.; Schaumann, E.

Authors: Bredenkamp, A.; Heimgartner, H.; Kantlehner, W.; Kirsch, S. F.; Kwiecień, H.; Lacôte, E.; Mlostoń, G.; Vallet, A.-L.; Wyatt, P. B.

Title: Knowledge Updates 2014/4

Print ISBN: 9783131763211; Online ISBN: 9783131975614; Book DOI: 10.1055/b-003-125861

1st edition © 2015 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry

Science of Synthesis Knowledge Updates



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

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Abstract

A comprehensive update of methods for the in situ generation of sulfonium ylides (sulfonium methanides, Corey–Chaykovsky reagents) and their applications for the synthesis of more complex molecules via methylene transfer is presented. Sulfonium ylides are widely applied in synthetically relevant reactions, such as cyclopropanation, aziridination, and epoxidation. Asymmetric versions of these processes are also summarized. In the presence of appropriate catalysts, preferably metal salts and/or complexes of gold or palladium, sulfonium ylides can undergo cascade heterocyclizations or C—H-insertion reactions.

Key words

asymmetric synthesis - aziridination - chemoselectivity - cyclopropanation - epoxidation - heterocycles - insertion reactions - sulfonium ylides - sulfur ylides
 
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