Diastereomeric fluoroolefins as peptide bond mimics prepared by asymmetric reductive amination of α-fluoroenones

被引：126

作者：

Dutheuil, Guillaume ^{[1
]}

Couve-Bonnaire, Samuel ^{[1
]}

Pannecoucke, Xavier ^{[1
]}

机构：

[1] INSA Rouen, CNRS, UMR 6014, ECOFH,IRCOF, F-76131 Mont St Aignan, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 08期

关键词：

asymmetric synthesis; fluoroenones; fluoroolefins; peptidomimetics; reductive amination;

D O I：

10.1002/anie.200604246

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Fluoropeptidomimetics: An efficient asymmetric reductive amination of fluoroenones has been developed that affords potential precursors of fluoropeptide isosteres. Stereoselective routes with different reductive agents provided both diastereomers from the same nonracemic sulfinyl imine. The method was applied to the synthesis of different dipeptide analogues. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：1290 / 1292

页数：3

共 38 条

[21] Asymmetric synthesis of syn- and anti-1,3-amino alcohols [J].

Kochi, T ;

Tang, TP ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (23) :6518-6519

[22] A facile and mild method for the synthesis of terminal bromofluoroolefins via diethylzinc-promoted Wittig reaction [J].

Lei, XS ;

Dutheuil, G ;

Pannecoucke, X ;

Quirion, JC .

ORGANIC LETTERS, 2004, 6 (13) :2101-2104

[23] Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones [J].

Liu, GC ;

Cogan, DA ;

Owens, TD ;

Tang, TP ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1278-1284

[24] Control of diastereoselectivity by solvent effects in the addition of Grignard reagents to enantiopure t-butylsulfinimine:: Syntheses of the Stereoisomers of the hydroxyl derivatives of sibutramine [J].

Lu, BZ ;

Senanayake, C ;

Li, NS ;

Han, ZX ;

Bakale, RP ;

Wald, SA .

ORGANIC LETTERS, 2005, 7 (13) :2599-2602

[25] STEREOSPECIFIC METHOD TO E-TERMINAL AND Z-TERMINAL FLUORO OLEFINS AND ITS APPLICATION TO THE SYNTHESIS OF 2'-DEOXY-2'-FLUOROMETHYLENE NUCLEOSIDES AS POTENTIAL INHIBITORS OF RIBONUCLEOSIDE DIPHOSPHATE REDUCTASE [J].

MCCARTHY, JR ;

MATTHEWS, DP ;

STEMERICK, DM ;

HUBER, EW ;

BEY, P ;

LIPPERT, BJ ;

SNYDER, RD ;

SUNKARA, PS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7439-7440

[26] An efficient synthetic method for Z-fluoroalkene dipeptide isosteres: Application to the synthesis of the dipeptide isostere of Sta-Ala [J].

Nakamura, Yuko ;

Okada, Midori ;

Koura, Minoru ;

Tojo, Manabu ;

Saito, Akio ;

Sato, Azusa ;

Taguchi, Takeo .

JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (4-5) :627-636

[27] A novel one-pot reaction involving organocopper-mediated reduction/transmetalation/asymmetric alkylation, leading to the diastereoselective synthesis of functionalized (Z)-fluoroalkene dipeptide isosteres [J].

Narumi, Tetsuo ;

Niida, Ayumu ;

Tomita, Kenji ;

Oishi, Shinya ;

Otaka, Akira ;

Ohno, Hiroaki ;

Fujii, Nobutaka .

CHEMICAL COMMUNICATIONS, 2006, (45) :4720-4722

[28] Enantioselective reduction of imines catalyzed by a rhenium(V)-oxo complex [J].

Nolin, KA ;

Ahn, RW ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (36) :12462-12463

[29]

Palacios F, 1998, EUR J ORG CHEM, V1998, P1413

[30] Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines:: switchover of diastereofacial selectivity [J].

Plobeck, N ;

Powell, D .

TETRAHEDRON-ASYMMETRY, 2002, 13 (03) :303-310

← 1 2 3 4 →