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Synthesis of optically active β- or γ-alkyl-substituted alcohols through copper-catalyzed asymmetric allylic alkylation with organolithium reagents.

The Journal of organic chemistry (2013-08-22)
Sureshbabu Guduguntla, Martín Fañanás-Mastral, Ben L Feringa
ABSTRACT

An efficient one-pot synthesis of optically active β-alkyl-substituted alcohols through a tandem copper-catalyzed asymmetric allylic alkylation (AAA) with organolithium reagents and reductive ozonolysis is presented. Furthermore, hydroboration-oxidation following the Cu-catalyzed AAA leads to the corresponding homochiral γ-alkyl-substituted alcohols.

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