The Effect of Water and Phenol on the Chiral Oxazaborolidine-Catalyzed Reduction of a Prostaglandin Enone Derivative
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- 作者：Chisa Ohta ; Shin-itsu Kuwabe ; Tai Shiraishi ; Shuichi Ohuchida ; Takuya Seko
- 刊名：Organic Process Research & Development
- 出版年：2009
- 出版时间：September 18, 2009
- 年：2009
- 卷：13
- 期：5
- 页码：933-935
- 全文大小：117K
- 年卷期：v.13,no.5(September 18, 2009)
- ISSN：1520-586X
文摘
The alcohol 2, a key intermediate in the synthesis of the highly selective EP4-receptor agonist ONO-4819, was synthesized by (R)-methyloxazaborolidine ((R)-Me-CBS)-catalyzed asymmetric reduction of enone 1 with borane dimethylsulfide complex. Addition of water and phenol to the reduction of enone 1 using (R)-Me-CBS as catalyst changed the chemoselectivity of the reduction.