Asymmetric enamide hydrogenation using phosphinite thioglycosides:: Synthesis of D- and L-aminoesters using D-sugars as catalyst precursors

被引：21

作者：

Khiar, Noureddine ^{[1
]}

Navas, Raquel ^{[1
]}

Suarez, Belen ^{[1
]}

Alvarez, Eleuterio ^{[1
]}

Fernandez, Inmaculada ^{[2
]}

机构：

[1] Univ Seville, CSIC, Inst Invest Quim, Seville 41092, Spain

[2] Univ Seville, Fac Farm, Dept Quim Organ & Farmaceut, E-41012 Seville, Spain

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 17期

关键词：

D O I：

10.1021/ol801301x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereomerically pure cationic Rh(I) complexes derived from phosphinite thioglycosides I were used as catalysts in highly enantioselective hydrogenations of enamides. The conformational similarity of alpha-D-arabinopyranose with beta-L-galactopyranose allows the synthesis of both enantiomers of alpha-amino acid derivatives such as D- and L-DOPA in excellent ee (97% and 98%), using derivatives of the former sugar as catalyst precursors.

引用

页码：3697 / 3700

页数：4

共 32 条

[1] THE STEREODYNAMICS OF METAL-COMPLEXES OF SULFUR-CONTAINING, SELENIUM-CONTAINING, AND TELLURIUM-CONTAINING LIGANDS [J].

ABEL, EW ;

BHARGAVA, SK ;

ORRELL, KG .

PROGRESS IN INORGANIC CHEMISTRY, 1984, 32 :1-118

[2] NUCLEAR-MAGNETIC-RESONANCE INVESTIGATIONS OF A NOVEL INTRAMOLECULAR METHYLTHIO REPLACEMENT PROCESS IN PALLADIUM(II) AND PLATINUM(II) COMPLEXES OF MIXED SULFUR PHOSPHINE-LIGANDS [J].

ABEL, EW ;

DORMER, JC ;

ELLIS, D ;

ORRELL, KG ;

SIK, V ;

HURSTHOUSE, MB ;

MAZID, MA .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1992, (06) :1073-1080

[3] TRANS-INFLUENCE - ITS MEASUREMENT AND SIGNIFICANCE [J].

APPLETON, TG ;

CLARK, HC ;

MANZER, LE .

COORDINATION CHEMISTRY REVIEWS, 1973, 10 (3-4) :335-422

[4]

AYERS TA, 1996, Patent No. 5510507

[5] Chiral P,S-ligands based on beta-d-thioglucose tetraacetate. Palladium(II) complexes and allylic alkylation [J].

Barbaro, P ;

Currao, A ;

Herrmann, J ;

Nesper, R ;

Pregosin, PS ;

Salzmann, R .

ORGANOMETALLICS, 1996, 15 (07) :1879-1888

[6] STRUCTURE AND REACTIVITY IN ASYMMETRIC HYDROGENATION - A MOLECULAR GRAPHICS ANALYSIS [J].

BROWN, JM ;

EVANS, PL .

TETRAHEDRON, 1988, 44 (15) :4905-4916

[7]

BROWN JM, 1999, HYDROGENATION FUNCTI, V1, P119

[8]

COBLEY CJ, ASYMMETRIC CATALYSIS, P269

[9] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

[10] Application of chiral mixed phosphorus/sulfur ligands to palladium-catalyzed allylic substitutions [J].

Evans, DA ;

Campos, KR ;

Tedrow, JS ;

Michael, FE ;

Gagné, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (33) :7905-7920

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