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Selektive Synthesen mit Organometallen II : Metallierung und Abwandlung funktionell substituierter Alkene
Author(s) -
Hartmann Jürgen,
Muthukrishnan Ramamurthi,
Schlosser Manfred
Publication year - 1974
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19740570744
Subject(s) - chemistry , alkene , medicinal chemistry , reagent , electrophile , selectivity , solvent , organic chemistry , catalysis
1,4‐Dienes, vinyl ethers, allyl ethers, allyl thioethers and propene‐thiolates are efficiently metalated by butyllithium in the presence of an activator such as potassium t ‐butoxide. Since the solvent, the counter‐ion or the temperature may be varied before subsequent treatment with an electrophilic reagent, the critical ratio of direct vs . vinylogous attack (substitution at the α‐ or γ‐position, respectively) can usually be adjusted within large limits. In many cases stereo‐selectivity is achieved as well.