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LDA‐Mediated Cascade Carbolithiation Reactions of Vinylidenecyclopropanes with Enones and N ‐Sulfonated Imines as well as Nitroalkene and (Phenylmethylidene)malononitrile
Author(s) -
Lu BeiLi,
Lu JianMei,
Shi Min
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101403
Subject(s) - nitroalkene , malononitrile , chemistry , cascade , adduct , computational chemistry , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , chromatography
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.