Synlett 2014; 25(5): 736-740
DOI: 10.1055/s-0033-1340628
letter
© Georg Thieme Verlag Stuttgart · New York

Nickel(0)-Promoted Carboxylation of Allenamides with Carbon Dioxide via a Nickelalactone Intermediate

Nozomi Saito*
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan   Fax: +81(11)7064982   eMail: biyo@pharm.hokudai.ac.jp
,
Yasuyuki Sugimura
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan   Fax: +81(11)7064982   eMail: biyo@pharm.hokudai.ac.jp
,
Yoshihiro Sato*
a   Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo 060-0812, Japan   Fax: +81(11)7064982   eMail: biyo@pharm.hokudai.ac.jp
b   ACT-C, Japan Science and Technology Agency (JST), Sapporo 060-0812, Japan
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Publikationsverlauf

Received: 21. November 2013

Accepted after revision: 18. Dezember 2013

Publikationsdatum:
29. Januar 2014 (online)


Abstract

Nickel(0)-promoted carboxylation of N-allenylamides (allenamides) with carbon dioxide proceeded via a nickelalactone intermediate to give β-amino acid derivatives. It was also found that the regioselectivity at the oxidative addition stage was strongly affected by the substituents on the allene part.

Supporting Information