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Regiospecific α‐Alkylation of α‐Haloalkylidenamines (“α‐Haloketimines”)
Author(s) -
De Kimpe Norbert,
Sulmon Paul,
Schamp Niceas
Publication year - 1985
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198508811
Subject(s) - alkylation , lithium diisopropylamide , halide , chemistry , alkyl , hydrogen , lithium (medication) , organic chemistry , medicinal chemistry , photochemistry , ion , catalysis , medicine , deprotonation , endocrinology
By masking α‐haloketones 1 as α‐haloalkylidenamines 2 , the α‐alkylation of haloketones becomes possible even when hydrogen atoms are present in the α′ position. The anions 3 , obtained by the use of lithium diisopropylamide, react with alkyl halides at room temperature to form exclusively C ‐alkylated products 4 .
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