Dynamic Kinetic Resolution: Asymmetric Transfer Hydrogenation of α-Alkyl-Substituted β-Ketoamides

被引：66

作者：

Limanto, John ^{[1
]}

Krska, Shane W. ^{[1
]}

Dorner, Benjamin T. ^{[1
]}

Vazquez, Enrique ^{[1
]}

Yoshikawa, Naoki ^{[1
]}

Tan, Lushi ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 03期

关键词：

HIGHLY STEREOSELECTIVE REDUCTION; ENANTIOSELECTIVE SYNTHESIS; HYDROXY ESTERS; KETO AMIDES; AMINO; CATALYSTS; LIGANDS; LACTAMS; ENZYMES; ROUTE;

D O I：

10.1021/ol902715d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Dynamic kinetic resolution (deracemization) of various alpha-alkyl-substituted beta-ketoamides 1 via asymmetric transfer hydrogenation proceeded efficiently to give the corresponding syn-beta-hydroxy amides 3 in high diastereo- and enantioselectivities. Specifically, subjection of 1 to HCO2H and Et3N in the presence of 0.5-1 mol % of pentafluorobenzenesulfonyl-DPEN-Ru catalyst 2b at 30-40 degrees C in either PhCH3 or CH2Cl2 generated the syn-hydroxy product 3 selectively in 15-33:1 dr, 93-97% ee, and 75-88% isolated yields.

引用

页码：512 / 515

页数：4

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