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Synlett 2001; 2001(Special Issue): 0991-0994
DOI: 10.1055/s-2001-14643
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Activation of C-H Bonds α to Nitriles for Combinatorial Chemistry: Ruthenium-Catalyzed Aldol and Michael Reactions of Polymer-Supported Nitriles

Hikaru Takaya* , Shun-Ichi Murahashi
  • *Department of Chemistry, Graduate School of Engineering Science, Osaka University, 1-3 Machikaneyama, Toyonaka, Osaka, 560-8531, Japan; Fax + 81-6-6850-6224; E-mail: mura@chem.es.osaka-u.ac.jp
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Publikationsdatum:
31. Dezember 2001 (online)

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Catalytic activation of C-H bonds adjacent to nitriles supported by Wang resin can be performed with ruthenium dihydride complex RuH2(PPh3)4 (1). Aldol and Michael reactions of the solid-supported cyanoacetates proceed to give the corresponding adducts in good yields under mild and neutral conditions. Four-component reactions that include sequential aldol-Michael-Michael reaction by C-H activation take place diastereoselectively.

ruthenium - C-H activations - solid-phase synthesis - nitriles - aldol reactions - Michael additions