Asymmetric Synthesis of the Roche Ester and its Derivatives by Rhodium‐INDOLPHOS‐Catalyzed Hydrogenation
Asymmetric Synthesis of the Roche Ester and its Derivatives by Rhodium‐INDOLPHOS‐Catalyzed Hydrogenation
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DOI：
10.1002/adsc.200800209
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发表时间：
2008-07
影响因子：
5.4
通讯作者：
J. Wassenaar;M. Kuil;J. Reek
中科院分区：
文献类型：
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作者：
J. Wassenaar;M. Kuil;J. Reek
以吲哚膦(diisopropyl{1-[(S)-3，5-dioxa-4-phosphacyclohepta[2，1-a；3，4-a]dinaphthalen-4-yl]-3-methyl-2-indolyl}phosphine)为手性配体，通过不对称催化氢化反应，成功地合成了(S)-3-羟基-2-甲基丙酸酯及其几个衍生物，产率很高，并且是迄今报道的最高的ee(25°C下TOF超过5500h-1；-40°C下可达98%ee)。
(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).