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Practical Synthesis of Allylic Silanes from Allylic Esters and Carbamates by Stereoselective Copper-Catalyzed Allylic Substitution Reactions

✍ Scribed by Martin Oestreich; Gertrud Auer

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 87 KB
Volume: 347
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200404381

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✦ Synopsis

The first copper-catalyzed allylic substitution reactions of allylic acetates and carbamates employing a bis(triorganosilyl)zinc reagent are reported. This novel procedure avoids the use of stoichiometric amounts of copper salts which are usually mandatory with this chemistry. Application of this methodology to standard model substrates substantiates a high diastereoselectivity for the double bond geometry (E : Z) as well as the relative configuration (syn : anti).

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