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Asymmetric Synthesis of the Roche Ester and its Derivatives by Rhodium‐INDOLPHOS‐Catalyzed Hydrogenation
Author(s) -
Wassenaar Jeroen,
Kuil Mark,
Reek Joost N. H.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200800209
Subject(s) - chemistry , rhodium , asymmetric hydrogenation , catalysis , phosphine , yield (engineering) , ligand (biochemistry) , medicinal chemistry , organic chemistry , enantioselective synthesis , receptor , biochemistry , materials science , metallurgy
( 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).