Synthesis 2014; 46(10): 1367-1373
DOI: 10.1055/s-0033-1340901
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric α-Allylation of α-Branched Aldehydes with Allyl Alcohols by Synergistic Catalysis Using an Achiral Palladium Complex and a Chiral Primary Amino Acid

Masanori Yoshida*
a   Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
b   Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   eMail: myoshida@eng.hokudai.ac.jp
,
Erika Masaki
b   Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   eMail: myoshida@eng.hokudai.ac.jp
,
Tatsuaki Terumine
b   Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   eMail: myoshida@eng.hokudai.ac.jp
,
Shoji Hara
a   Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan
b   Molecular Chemistry and Engineering Course, Graduate School of Chemical Sciences and Engineering, Hokkaido University, Kita 13-jo Nishi 8, Kita-ku, Sapporo, Hokkaido 060-8628, Japan   Fax: +81(11)7066557   eMail: myoshida@eng.hokudai.ac.jp
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Publikationsverlauf

Received: 26. Dezember 2013

Accepted after revision: 12. Februar 2014

Publikationsdatum:
17. März 2014 (online)


Abstract

Highly enantioselective direct α-allylation of α-branched aldehydes with simple allyl alcohols was achieved by the combined use of an achiral transition-metal catalysis with a palladium complex and a chiral organocatalysis with a readily obtainable primary α-amino acid. Various α-allylated aldehydes possessing a stereocontrolled quaternary carbon stereogenic center were synthesized in high yields with high enantioselectivity.

Supporting Information

 
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