- Dynamic Kinetic Asymmetric Reductive Amination: Synthesis of Chiral Primary β-Amino Lactams
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A highly efficient ruthenium-catalyzed asymmetric reductive amination (ARA) of racemic β-keto lactams with molecular hydrogen and ammonium salts is disclosed for the synthesis of enantiomerically pure primary amino lactams through dynamic kinetic resolution (DKR). By this approach, a range of syn primary β-amino lactams were obtained in high yields with high chemo-, enantio-, and diastereoselectivity (up to 98 % yield, 99 % ee, >20:1 d.r., syn products). The utility of the products has been demonstrated by rapid access to a key synthetic intermediate towards biologically active drug molecules. Meanwhile, mechanistic studies and control experiments indicate that the reaction may proceed through the hydrogenation of an iminium intermediate.
- Lou, Yazhou,Hu, Yutao,Lu, Jiaxiang,Guan, Fanfu,Gong, Gelin,Yin, Qin,Zhang, Xumu
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supporting information
p. 14193 - 14197
(2018/10/15)
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- METHOD FOR PRODUCING A RUTHENIUM COMPLEX
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Provided is a method for producing a ruthenium complex comprises the step of reacting a ruthenium compound represented by general formula (1): [in-line-formulae][RuX(L)(PP)]X ??(1),[/in-line-formulae] wherein Ru represents a ruthenium atom; X represents a halogen atom; L represents an arene; and PP represents an optically active bisphosphine, with a carboxylate salt represented by general formula (2): [in-line-formulae]R1CO2M ??(2),[/in-line-formulae] wherein M represents a monovalent cation; and R1 represents a group selected from the group consisting of alkyl groups, haloalkyl groups, phenyl groups optionally having a substituent(s), 1-aminoalkyl groups and 1-amino-1-phenylalkyl groups, to produce a ruthenium complex represented by general formula (3): [in-line-formulae]Ru(OCOR1)2(PP) ??(3),[/in-line-formulae] wherein R1 represents the group selected from the group consisting of alkyl groups, haloalkyl groups, phenyl groups optionally having a substituent(s), 1-aminoalkyl groups and 1-amino-1-phenylalkyl groups; and PP represents the optically active bisphosphine.
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Page/Page column 7
(2010/04/23)
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