Asymmetric Synthesis of anti-β-Amino-α-Hydroxy Esters via Dynamic Kinetic Resolution of β-Amino-α-Keto Esters

被引：69

作者：

Goodman, C. Guy ^{[1
]}

Do, Dung T. ^{[1
]}

Johnson, Jeffrey S. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem, Chapel Hill, NC 27599 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 10期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; TAXOL SIDE-CHAIN; TRANSFER HYDROGENATION; STEREOSELECTIVE-SYNTHESIS; ACID-DERIVATIVES; CHLORAMINE-T; OLEFINS; ALDEHYDES; AMINOHYDROXYLATION; INHIBITOR;

D O I：

10.1021/ol4009206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for the asymmetric synthesis of enantioenriched anti-alpha-hydroxy-beta-amino acid derivatives by enantioconvergent reduction of the corresponding racemic alpha-keto esters is presented. The requisite alpha-keto esters are prepared via Mannich addition of ethyl diazoacetate to imines followed by oxidation of the diazo group with Ozone. Implementation of a recently developed dynamic kinetic resolution of beta-substituted-alpha-keto esters via Ru(II)-catalyzed asymmetric transfer hydrogenation provides the title motif in routinely high diastereo- and enantioselectivity.

引用

页码：2446 / 2449

页数：4

共 47 条

[1] A highly efficient synthesis of the C-13 side-chain of taxol using Shibasaki's asymmetric Henry reaction [J].

Borah, JC ;

Gogoi, S ;

Boruwa, J ;

Kalita, B ;

Barua, NC .

TETRAHEDRON LETTERS, 2004, 45 (18) :3689-3691

[2] Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].

Cardillo, G ;

Tomasini, C .

CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&

[3] Diametric Stereocontrol in Dynamic Catalytic Reduction of Racemic Acyl Phosphonates: Divergence from α-Keto Ester Congeners [J].

Corbett, Michael T. ;

Johnson, Jeffrey S. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (02) :594-597

[4] A PRACTICAL, HIGHLY ENANTIOSELECTIVE SYNTHESIS OF THE TAXOL SIDE-CHAIN VIA ASYMMETRIC CATALYSIS [J].

DENG, L ;

JACOBSEN, EN .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4320-4323

[5] Catalytic Asymmetric Cross-Aza-Benzoin Reactions of Aliphatic Aldehydes with N-Boc-Protected Imines [J].

DiRocco, Daniel A. ;

Rovis, Tomislav .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5904-5906

[6] Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready α-hydroxy-β-amino acids [J].

Dziedzic, Pawel ;

Vesely, Jan ;

Cordova, Armando .

TETRAHEDRON LETTERS, 2008, 49 (47) :6631-6634

[7] Highly Enantioselective Organocatalytic Addition of Aldehydes to N-(Phenylmethylene)benzamides: Asymmetric Synthesis of the Paclitaxel Side Chain and Its Analogues [J].

Dziedzic, Pawel ;

Schyman, Patric ;

Kullberg, Martin ;

Cordova, Armando .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (16) :4044-4048

[8] KRI-1314-AN ORALLY EFFECTIVE INHIBITOR OF HUMAN RENIN [J].

ETOH, Y ;

MIYAZAKI, M ;

SAITOH, H ;

TODA, N .

JAPANESE JOURNAL OF PHARMACOLOGY, 1993, 63 (01) :109-119

[9] First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water.: A new protocol for preparation of optically active norstatines [J].

Fringuelli, F ;

Pizzo, F ;

Rucci, M ;

Vaccaro, L .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7041-7045

[10] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].

Fujii, A ;

Hashiguchi, S ;

Uematsu, N ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522

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