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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