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Zeolites in the Synthesis of Terpenyl Amines By Isoprene Telomerization, pp. 625-636 $100.00
Authors:  (E.A. Petrushkina, D.V. Khomishin, N.E. Mysova, A.V. Orlinkov, V.N. Kalinin, Ya.V. Zubavichus, A.A. Veligzhanin - Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow, Russia and others)
Abstract:
The telomerization of 1,3-dienes with nucleophiles catalyzed by transition metals is an
example of the environmentally benign synthetic method. Easily available starting materials
are converted in the presence of a catalyst to functionalized octa-2,7-dienes in a 100% atom
efficient manner [1, 2]. The use of isoprene in this reaction offers attractive routes to various
terpenoid derivatives. The isoprene coupling can occur in a tail-to-tail (t-t), tail-to-head (t-h),
head-to-head (h-h) and head-to-tail (h-t) manners (Scheme 1). Along with the 1-substituted
2:1 telomers, 3-substituted products of the same carbon skeleton, 1:1 adducts, and nonsubstituted
trienes can be obtained as by-products (Scheme 1). The fractions of possible
products depend on the nature of the nucleophile, solvent, temperature and catalyst employed.
In the case of alcohols as nucleophiles, only modest selectivity is usually achieved with tailto-
head or tail-to-tail telomers dominating. Meanwhile, in the case of amines, all possible
skeleton isomers are afforded [3] and the selection of appropriate palladium complex, ligand,
solvent and acid enabled the 60-98% selectivity for the t-t telomer [4], the 56-89% selectivity
for the t-h telomer [5] and the 73-97% selectivity for the h-h telomer [6]. The worst
selectivity of only 40-41% [4c, 5a] was achieved for the h-t telomer with the naturally
occurring structure of α-geranylamine. 


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Zeolites in the Synthesis of Terpenyl Amines By Isoprene Telomerization, pp. 625-636