Efficient parallel resolution of racemic Evans' oxazolidinones using quasi-enantiomeric profens

被引：27

作者：

Coumbarides, GS

Dingjan, M

Eames, J

Flinn, A

Motevalli, M

Northen, J

Yohannes, Y

机构：

[1] Queen Mary Univ London, Dept Chem, London E1 4NS, England

[2] Onyx Sci Ltd, Sunderland SR5 2TQ, England

来源：

SYNLETT | 2006年 / 01期

关键词：

chiral auxiliaries; chiral resolution; kinetic resolution; molecular recognition; stereoselectivity;

D O I：

10.1055/s-2005-922784

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Racemic Evans' oxazolidinones were efficiently resolved using a combination of quasi-enantiomeric profens. The levels of stereocontrol were high, giving products with predictable configurations.

引用

页码：101 / 105

页数：5

共 17 条

[1] UNLIMITED NONLINEAR SELECTIVITY EFFECTS IN SYSTEMS OF INDEPENDENT PARALLEL REACTIONS AS A BASIS FOR NEW CHEMICAL SEPARATION TECHNIQUES [J].

BRANDT, J ;

JOCHUM, C ;

UGI, I .

TETRAHEDRON, 1977, 33 (11) :1353-1363

[2] Efficient parallel resolution of an active ester of 2-phenylpropionic acid using quasi-enantiomeric Evans' oxazolidinones [J].

Coumbarides, GS ;

Dingjan, M ;

Eames, J ;

Flinn, A ;

Northen, J ;

Yohannes, Y .

TETRAHEDRON LETTERS, 2005, 46 (16) :2897-2902

[3] Probing the resolution of 2-phenylpropanoyl chloride using quasi-enantiomeric Evans' oxazolidinones [J].

Coumbarides, GS ;

Eames, J ;

Flinn, A ;

Northen, J ;

Yohannes, Y .

TETRAHEDRON LETTERS, 2005, 46 (05) :849-853

[4] Parallel kinetic resolution of tert-butyl (RS)-3-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl-cispentacin derivatives [J].

Davies, SG ;

Garner, AC ;

Long, MJC ;

Smith, AD ;

Sweet, MJ ;

Withey, JM .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (22) :3355-3362

[5] Preparation of methyl (1R,2S,5S)- and (1S,2R,5R)-2-amino-5-tert-butyl-cyclopentane-l-carboxylates by parallel kinetic resolution of methyl (RS)-5-tert-butyl-cyclopentene-l-carboxylate [J].

Davies, SG ;

Díez, D ;

El Hammouni, MM ;

Garner, AC ;

Garrido, NM ;

Long, MJC ;

Morrison, RM ;

Smith, AD ;

Sweet, MJ ;

Witheya, JCM .

CHEMICAL COMMUNICATIONS, 2003, (19) :2410-2411

[6] Parallel kinetic resolution of racemic mixtures: a new strategy for the preparation of enantiopure compounds? [J].

Dehli, JR ;

Gotor, V .

CHEMICAL SOCIETY REVIEWS, 2002, 31 (06) :365-370

[7]

Eames J, 2000, ANGEW CHEM INT EDIT, V39, P885, DOI 10.1002/(SICI)1521-3773(20000303)39:5<885::AID-ANIE885>3.0.CO

[8]

2-2

[9] Resolution of enantiomers by non-conventional methods [J].

Fogassy, E ;

Nógrádi, M ;

Pálovics, E ;

Schindler, J .

SYNTHESIS-STUTTGART, 2005, (10) :1555-1568

[10] Copper(II)-catalyzed kinetic resolution of (±)-2-arylpropionic acids with chiral N-trimethylsilyloxazolidin-2-one [J].

Fukuzawa, S ;

Chino, Y ;

Yokoyama, T .

TETRAHEDRON-ASYMMETRY, 2002, 13 (15) :1645-1649

← 1 2 →