Catalytic C-C double bond cleavage of α,β-enones with a 1-alkene and H2O was carried out in the presence of a (Ph3P)3RhCl catalyst, 2-amino-3-picoline, cyclohexylamine, benzoic acid, and alkyl group-immobilized silica spheres. Upon completion of the reaction, the corresponding ketones were obtained without needing a further hydrolysis step. In this reaction, alkyl group-immobilized silica spheres act as a water reservoir for hydrolysis of an intermediate ketimine and as a phase divider between the organic solution and H2O.
Bibliographical noteFunding Information:
This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) ( KRF-2008-313-C00483 ), the WCU (World Class University) program through the Korea Science and Engineering Foundation funded by the Ministry of Education, Science and Technology ( R32-2008-000-10217-0 ) and the CBMH. D.H.L. and J.W.P. acknowledge the fellowships from the BK21 program of the Ministry of Education and Human Resources Development.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry