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Stereoselective Transformations of α‐Trifluoromethylated Ketoximes to Optically Active Amines by Enzyme–Nanometal Cocatalysis: Synthesis of ( S )‐Inhibitor of Phenylethanolamine N‐Methyltransferase
Author(s) -
Cheng Guilin,
Wu Qi,
Shang Zeyu,
Liang Xinhua,
Lin Xianfu
Publication year - 2014
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201402114
Subject(s) - enantiopure drug , chemistry , phenylethanolamine , catalysis , hydrolysis , amine gas treating , lipase , stereoselectivity , candida antarctica , organic chemistry , optically active , silanes , enantioselective synthesis , combinatorial chemistry , enzyme , silane , tyrosine hydroxylase
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.