Palladium-Catalyzed Asymmetric Amination and Imidation of 2,3-Allenyl Phosphates

Yasushi Imada,* Masayuki Nishida, Koji Kutsuwa, Shun-Ichi Murahashi,*† and Takeshi Naota*; ;
Department of Chemistry, Graduate School of Engineering Science, Osaka University Machikaneyama, Toyonaka, Osaka 560-8531, Japan
Org. Lett., 2005, 7 (26), pp 5837–5839
DOI: 10.1021/ol0523502
Publication Date (Web): December 1, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Present address:  Department of Applied Chemistry, Faculty of Engineering, Okayama University of Science, Ridaicho, Okayama, Okayama 700-0005, Japan.

, imada@chem.es.osaka-u.ac.jp, ; , murahashi@high.ous.ac.jp, ; , naota@chem.es.osaka-u.ac.jp

Abstract

Abstract Image

Asymmetric amination of 2,3-allenyl phosphates with nitrogen nucleophiles such as amines, hydroxylamines, and imides can be performed efficiently using a combination of zerovalent palladium complexes and SEGPHOS or MeOBIPHEP ligand, affording the corresponding optically active 1-aminated derivatives with enantiomeric excess of up to 97% ee.

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History

  • Published In Issue December 22, 2005
  • Received September 28, 2005

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