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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
Author(s) -
Afewerki Samson,
Breistein Palle,
Pirttilä Kristian,
Deiana Luca,
Dziedzic Pawel,
Ibrahem Ismail,
Córdova Armando
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201100756
Subject(s) - enantioselective synthesis , catalysis , alkylation , chemistry , organic chemistry , amine gas treating
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 (see scheme). The methodology was applied to the short total syntheses of bisabolane sesquiterpenes ( S )‐(+)‐curcumene, ( E )‐( S )‐(+)‐3‐dehydrocurcumene and ( S )‐(+)‐tumerone.