Stereoselective Transformations of α‐Trifluoromethylated Ketoximes to Optically Active Amines by Enzyme–Nanometal Cocatalysis: Synthesis of ( S)‐Inhibitor of Phenylethanolamine N‐Methyltransferase

• Published in: ChemCatChem
• Main Authors: Cheng, Guilin, Wu, Qi, Shang, Zeyu, Liang, Xinhua, Lin, Xianfu
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2014
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/cctc.201402114; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcctc.201402114; https://onlinelibrary.wiley.com/doi/full/10.1002/cctc.201402114

Abstract One‐pot cascade synthesis of optically active α‐trifluoromethylated amines directly from ketoximes was accomplished with the use of Candida antarctica lipase B and catalysts prepared by atomic layer deposition (ALD). Compared to the commercial palladium catalyst, the ALD‐prepared catalysts showed much higher activity and afforded various α‐trifluoromethylated amides in good yields and with high enantioselectivity. One of the enantiopure amides was further hydrolyzed into the corresponding amine, which was treated as a crucial starting material for total synthesis of ( S )‐inhibitor of phenylethanolamine N‐methyltransferase without loss of chiral information.