Synthesis 2017; 49(06): 1295-1300
DOI: 10.1055/s-0036-1588095
paper
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Allylation of 2-Oxocycloalkanecarboxylates

Masanori Yoshida*
a   Faculty of Mathematics and Science, National Institute of Technology, Asahikawa College, 2-1-6, Shunko-dai 2-jo, Asahikawa, Hokkaido 071-8142, Japan
,
Shohei Yano
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   Email: yoshida@edu.asahikawa-nct.ac.jp
,
Shoji Hara
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   Email: yoshida@edu.asahikawa-nct.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 24 September 2016

Accepted: 21 October 2016

Publication Date:
24 November 2016 (online)


Abstract

In this study, the highly enantioselective α-allylation of α-substituted β-ketoesters, particularly 2-oxocycloalkanecarboxylates, is achieved by synergistic catalysis with an achiral palladium complex and a chiral primary amino acid. Various α-allylated β-ketoesters containing a quaternary carbon stereogenic center are synthesized in high yields (up to 97%) with excellent enantioselectivity (up to 99% ee).

Supporting Information