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

共 46 条

[1] β-lactams:: Versatile building blocks for the stereoselective synthesis of non-β-lactam products
Alcaide, Benito
Almendros, Pedro
Aragoncillo, Cristina
[J]. CHEMICAL REVIEWS, 2007, 107 (11) : 4437 - 4492
[2] Dynamic kinetic resolution-asymmetric transfer hydrogenation of 1-aryl-substituted cyclic ketones
Alcock, NJ
Mann, I
Peach, P
Wills, M
[J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (22) : 2485 - 2490
[3] Highly stereoselective reduction of β-keto amides:: The first general and efficient approach to N-mono- and non-substituted anti-α-alkyl β-hydroxy amides
Bartoli, G
Bosco, M
Marcantoni, E
Melchiorre, P
Rinaldi, S
Sambri, L
[J]. SYNLETT, 2004, (01) : 73 - 76
[4] One-pot highly stereoselective reduction of β-keto amides to syn-γ-aminols
Bartoli, G
Bosco, M
Dalpozzo, R
Marcantoni, E
Massaccesi, M
Rinaldi, S
Sambri, L
[J]. TETRAHEDRON LETTERS, 2001, 42 (50) : 8811 - 8815
[5] STUDIES ON LACTAMS .70. STEREOSPECIFIC CYCLIZATION OF BETA-HYDROXY ARYL AMIDES TO BETA-LACTAMS
BOSE, AK
MANHAS, MS
SAHU, DP
HEGDE, VR
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1984, 62 (11): : 2498 - 2505
[6] Novel syntheses of azetidines and azetidinones
Brandi, Alberto
Cicchi, Stefano
Cordero, Franca M.
[J]. CHEMICAL REVIEWS, 2008, 108 (09) : 3988 - 4035
[7] *CCDC, 752316 CCDC
[8] 2-azetidinone cholesterol absorption inhibitors: Structure-activity relationships on the heterocyclic nucleus
Clader, JW
Burnett, DA
Caplen, MA
Domalski, MS
Dugar, S
Vaccaro, W
Sher, R
Browne, ME
Zhao, HR
Burrier, RE
Salisbury, B
Davis, HR
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (19) : 3684 - 3693
[9] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes
Clapham, SE
Hadzovic, A
Morris, RH
[J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2201 - 2237
[10] Inhibition of human cytomegalovirus protease No with monocyclic β-lactams
Déziel, R
Malenfant, E
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (11) : 1437 - +

← 1 2 3 4 5 →