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LDA-Mediated Cascade Carbolithiation Reactions of Vinylidenecyclopropanes with Enones and N-Sulfonated Imines as well as Nitroalkene and (Phenylmethylidene)malononitrile

✍ Scribed by Bei-Li Lu; Jian-Mei Lu; Min Shi


Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
710 KB
Volume
2012
Category
Article
ISSN
1434-193X

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✦ Synopsis


Abstract

LDA‐mediated cascade carbolithiation reactions of vinylidenecyclopropanes with enones and N‐sulfonated imines as well as nitroalkene and (phenylmethylidene)malononitrile in THF at –78 °C have been realized; the corresponding novel adducts were produced in moderate to good yields with moderate to high diastereoselectivities. The scope and limitations are discussed as well as a plausible reaction mechanism based on control experiments performed in this work and previous literature reports.