A new look at boron enolate chemistry: aminative C-C bond formation using diaminoboron enolate with aldehyde

Michinori Suginome; Lars Uehlin; Akihiko Yamamoto; Masahiro Murakami

doi:10.1021/ol0497436

A new look at boron enolate chemistry: aminative C-C bond formation using diaminoboron enolate with aldehyde

Org Lett. 2004 Apr 1;6(7):1167-9. doi: 10.1021/ol0497436.

Authors

Michinori Suginome¹, Lars Uehlin, Akihiko Yamamoto, Masahiro Murakami

Affiliation

¹ Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan. suginome@sbchem.kyoto-u.ac.jp

PMID: 15040749
DOI: 10.1021/ol0497436

Abstract

Unlike ordinary boron enolates, such as dialkylboryl (R(2)B) and dialkoxyboryl ((RO)(2)B) derivatives, reactions of diaminoboryl ((R(2)N)(2)B) enolates with aldehydes proceed with the concurrent transfer of amino and enoxy groups from the boron to the aldehyde carbon, yielding beta-amino ketones in a selective manner.