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Asymmetric palladium-assisted alkylation of olefins

✍ Scribed by A. Solladié-Cavallo; J.L. Haesslein; Jan-E. Bäckvall

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
207 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

Palladrum-promoted alkylatron of some alkenes using choral sulfoxidecontalnmg carbanlon as nucleophlles or using optrcally active N,N-dlmethyl-u--phenylethylamlne as ligand together with a non-choral stabilized carbanlon as nucleophlle results in an asymmetric Induction of 10-40X. Palladlunrasslsted nucleophllic addrtlons to olefrns are well known and of particular Interest in organic synthesis. 192 During work on transition-metal asslsted asymmetric synthesis 3 we became Interested in the posslblllty of inducing asymmetry in the nucleophrlrc addition of stabilrsed carbanlons to n-oleflnpalladlum complexes. Asymmetric induction has previously been observed in the palladium-catalyzed cycllzatlon of 2-allyl-phenol4 and rn the nucleophilic addition of stablllzed carbanron to r-allylpalladlum complexes. 5

In the preceeding communication we have shown that an asymmetric induction was obtained in the palladium-promoted oxyamlnatlon of oleflns.

6 We now report some results from palladrum-promoted asymmetrrc alkylatron of oleflns.

The general accepted route for palladium-assisted alkylation is shown m Scheme 1.

Scheme 1.

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