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Asymmetric Hydrogenation of 2,4-Dioxo Esters: Selective Synthesis of 2-Hydroxy-4-oxo Esters and Direct Access to Chiral 2-Hydroxy-4-butyrolactones

✍ Scribed by Véronique Blandin; Jean-François Carpentier; André Mortreux

Publisher: John Wiley and Sons
Year: 1999
Tongue: English
Weight: 263 KB
Volume: 1999
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199908)1999:8<1787::aid-ejoc1787>3.0.co;2-o

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✦ Synopsis

Ve ´ronique Blandin, [a] Jean-Franc ¸ois Carpentier,* [a] and Andre ´Mortreux [a] Keywords: Asymmetric synthesis / Hydrogenations / Ketones / Chiral α-hydroxy-γ-butyrolactones / Chiral α-hydroxy-γoxo esters 2,4-Dioxoesters 1a-c are selectively converted into optically hydroxy-4-butyrolactones 4a-c proceeds in high yields; catalytic activities, chemo-, dia-, and enantioselectivities are active 2-hydroxy-4-oxoesters 2a-c by hydrogenation with chiral rhodium-aminophosphane-phosphinite catalysts (82-strongly dependant upon the nature of the substrate and the catalyst. 88% ee) or ruthenium-bisphosphane catalysts (52-67% ee). Direct one-pot hydrogenation of 2,4-dioxoesters 1a-c to 2- [a]

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