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Lithium Diisopropylamide‐Mediated Carbolithiation Reactions of Vinylidenecyclopropanes and Further Transformations of the Adducts
Author(s) -
Lu JianMei,
Shi Min
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200900068
Subject(s) - lithium diisopropylamide , regioselectivity , electrophile , adduct , chemistry , lewis acids and bases , lithium (medication) , organic chemistry , medicinal chemistry , catalysis , medicine , ion , deprotonation , endocrinology
Synthetic methods : Lithium diisopropylamide‐mediated highly selective carbolithiation reactions of vinylidenecyclopropanes are described and further transformations of these adducts were performed in the presence of Lewis or Brønsted acids (see scheme for sample reactions).Highly stereo‐ and regioselective carbolithiation reactions of vinylidenecyclopropanes 1 were realized by treatment with lithium diisopropylamide (LDA) in THF and by quenching with various electrophiles such as aryl or aliphatic aldehydes, ketones, enones or propargyl bromide. Transformation of these adducts such as vinylcyclopropenes and allenols was also performed in the presence of Lewis acid or Brønsted acid to provide the fused and conjugated aromatic products in good to high yields under mild conditions.