Asymmetric syntheses of (1r,3R,4S)- and (1s,3R,4S)-(3,4-difluorocyclopentyl)-alanine derivatives

被引：3

作者：

Simpson, Robert D. ^{[1
]}

Zhao, Wei ^{[1
]}

机构：

[1] Vitae Pharmaceut, Dept Chem, Ft Washington, PA 19034 USA

来源：

TETRAHEDRON-ASYMMETRY | 2009年 / 20卷 / 13期

关键词：

ENANTIOSELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; FLUORINE; DISCOVERY; POTENT;

D O I：

10.1016/j.tetasy.2009.05.024

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

By employing a sequence of epoxide opening, asymmetric alkylation, and fluorination, polyfluorinated cyclopentylamino acids with defined stereochemistries were prepared. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1515 / 1520

页数：6

共 30 条

[1] Pd-catalyzed asymmetric hydrogenation of α-fluorinated iminoesters in fluorinated alcohol:: A new and catalytic enantioselective synthesis of fluoro α-amino acid derivatives [J].

Abe, H ;

Amii, H ;

Uneyama, K .

ORGANIC LETTERS, 2001, 3 (03) :313-315

[2] BOND LENGTH AND REACTIVITY - THE GAUCHE EFFECT - A COMBINED CRYSTALLOGRAPHIC AND THEORETICAL INVESTIGATION OF THE EFFECTS OF BETA-SUBSTITUENTS ON C-OX BOND LENGTH [J].

AMOS, RD ;

HANDY, NC ;

JONES, PG ;

KIRBY, AJ ;

PARKER, JK ;

PERCY, JM ;

SU, MD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :549-558

[3] A short and efficient synthesis of L-5,5,5,5',5',5'-hexafluoroleucine from N-Cbz-L-serine [J].

Anderson, JT ;

Toogood, PL ;

Marsh, ENG .

ORGANIC LETTERS, 2002, 4 (24) :4281-4283

[4] REACTION OF POTASSIUM FLUORIDE WITH ALPHA-FLUORINATED TOSYLATES - SYNTHESIS AND PROPERTIES OF 1,2-DIFLUORINATED DERIVATIVES [J].

BAKLOUTI, A ;

ELGHARBI, R .

JOURNAL OF FLUORINE CHEMISTRY, 1979, 13 (04) :297-314

[5] Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products [J].

Begue, Jean-Pierre ;

Bonnet-Delpon, Daniele .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (08) :992-1012

[6] Contribution to the study of the Gauche effect. The complete structure of the anti rotamer of 1,2-difluoroethane [J].

Craig, NC ;

Chen, A ;

Suh, KH ;

Klee, S ;

Mellau, GC ;

Winnewisser, BP ;

Winnewisser, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (20) :4789-4790

[7] Efficient asymmetric synthesis of β-fluoro α-amino acids [J].

Davis, FA ;

Srirajan, V ;

Titus, DD .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) :6931-6934

[8] SYNTHESIS AND RESOLUTION OF 3-FLUORO-D,L-ALANINE-2-D - SELECTIVE DEUTERATION VIA REDUCTIVE AMINATION WITH SODIUM BORODEUTERIDE [J].

DOLLING, UH ;

DOUGLAS, AW ;

GRABOWSKI, EJJ ;

SCHOENEWALDT, EF ;

SOHAR, P ;

SLETZINGER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (09) :1634-1640

[9] Enantioselective synthesis of fluorinated α-amino acids and derivatives in combination with ring-closing metathesis:: Intramolecular π-stacking interactions as a source of stereocontrol [J].

Fustero, S ;

Navarro, A ;

Pina, B ;

Soler, JG ;

Bartolomé, A ;

Asensio, A ;

Simón, A ;

Bravo, P ;

Fronza, G ;

Volonterio, A ;

Zanda, M .

ORGANIC LETTERS, 2001, 3 (17) :2621-2624

[10] Mechanism and applications of lithium amide-induced asymmetric rearrangements of 4-substituted and 4,4-disubstituted cyclopentene oxides to cyclopentenols [J].

Hodgson, DM ;

Gibbs, AR ;

Drew, MGB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (24) :3579-3590

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