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Catalytic enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes
Journal article   Peer reviewed

Catalytic enantioselective β-alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes

Samson Afewerki, Palle Breistein, Kristian Pirttilä, Luca Deiana, Pawel Dziedzic, Ismail Ibrahem and Armando Córdova
Chemistry : a European journal, Vol.17(32), pp.8784-8788
01/08/2011
DOI: https://doi.org/10.1002/chem.201100756
PMID: 21732445

Abstract

Aldehydes - chemistry Alkylation Catalysis Molecular Structure Sesquiterpenes - chemical synthesis Sesquiterpenes - chemistry Stereoisomerism Transition Elements - chemistry
Branching out! The first co-catalytic enantioselective (up to 98:2 e.r.) β-alkylation of α,β-unsaturated aldehydes by combination of simple chiral amine and copper catalysts provides β-branched aldehydes in a one-pot protocol. The methodology was applied to the short total syntheses of bisabolane sesquiterpenes (S)-(+)-curcumene, (E)-(S)-(+)-3-dehydrocurcumene and (S)-(+)-tumerone.

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