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Asymmetric Synthesis of the Roche Ester and its Derivatives by Rhodium-INDOLPHOS-Catalyzed Hydrogenation

✍ Scribed by Jeroen Wassenaar; Mark Kuil; Joost N. H. Reek


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
178 KB
Volume
350
Category
Article
ISSN
1615-4150

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✦ Synopsis


Abstract

(S)‐3‐Hydroxy‐2‐methylpropionate, known as the Roche ester, and several of its derivatives were successfully synthesized through asymmetric rhodium‐catalyzed hydrogenation, using INDOLPHOS (diisopropyl{1‐[(S)‐3,5‐dioxa‐4‐phosphacyclohepta[2,1‐a;3,4‐a′]dinaphthalen‐4‐yl]‐3‐methyl‐2‐indolyl}phosphine) as the chiral ligand, in excellent yield and the highest ee reported up to now (TOF over 5500 h^−1^ at 25 °C; up to 98% ee at −40 °C).


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