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2005
Cyclopentane derivatives
Q 0030
Tandem Intramolecular Carbolithiation-Lithium/Zinc Transmetallation and Apto Carbon—Carbon Bond-Forming Reactions. — Intramolecular carbo01- 068 plications
lithiation of 6-chlorohexene (I) followed by cyclization and lithium/zinc transmetallation gives the organozinc reagent (II). After activation with transition metal complexes
such as those derived from copper or palladium, it undergoes a series of SN2' reactions
with allylic or propargylic halides as well as arylation, vinylation, benzylation, acylation and conjugate addition to α,β-unsaturated carbonyl compounds. After hydrolysis,
a series of C-C coupled products are obtained which are not directly accessible from
the organolithium precursor even with transition metal catalysis. — (YUS*, M.;
ORITZ, R.; Eur. J. Org. Chem. 2004, 18, 3833-3841; Dep. Quim. Org., Fac. Cienc.,
Univ. Alicante, E-03080 Alicante, Spain; Eng.) — Kieslich
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