Catalytic Four-Component Assembly Based on Allenylboronate Platform:  New Access to Privileged Allylic Amine Structures

Keisuke Tonogaki,† Kenichiro Itami,*‡§ and Jun-ichi Yoshida*†;
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan, and Research Center for Materials Science, Nagoya University, Nagoya 464-8602, Japan
J. Am. Chem. Soc., 2006, 128 (5), pp 1464–1465
DOI: 10.1021/ja057778a
Publication Date (Web): January 12, 2006
Copyright © 2006 American Chemical Society
†

 Kyoto University.

,
*

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

,
‡

 Nagoya University.

,
§

 PRESTO, Japan Science and Technology Agency (JST).

, itami@chem.nagoya-u.ac.jp, ; , yoshida@sbchem.kyoto-u.ac.jp

Abstract

Abstract Image

We developed a novel palladium-catalyzed four-component assembly based on allenylboronate platform, by which privileged allylic amine structures can be constructed in a regioselective, stereoselective, and diversity-oriented manner. The boryl group acts not only as a useful group that can be transformed to various functional groups afterward but also as a stereochemical controller in the generation of key (π-allyl)palladium intermediates. A short synthesis of rolipram (selective phosphodiesterase-4 inhibitor) is also demonstrated.

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History

  • Published In Issue February 08, 2006
  • Received November 16, 2005

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