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Reductive aldol coupling of divinyl ketones via rhodium-catalyzed hydrogenation: Syn-diastereoselective construction of β-hydroxyenones

Organic Letters, ISSN: 1523-7060, Vol: 8, Issue: 24, Page: 5657-5660
2006
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Article Description

Catalytic hydrogenation of divinyl ketones 1a and 1e in the presence of diverse aldehydes 2a-e at ambient temperature and pressure using cationic rhodium catalysts ligated by tri-2-furyl phosphine enables formation of aldol products 3a-e and 5a-e, respectively, with high levels of syn diastereoselection. Through an assay of counterions (Rh(COD)X), Rh(COD)SbF is identified as the optimum precatalyst for reductive aldol couplings of this type. For para-substituted styryl vinyl ketones 1b-e, a progressive increase in isolated yield is observed for electron-releasing para substituents. © 2006 American Chemical Society.

Bibliographic Details

Han, Soo Bong; Krische, Michael J

American Chemical Society (ACS)

Biochemistry, Genetics and Molecular Biology; Chemistry

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