Diastereoselective conjugate addition of cyanide to α,β-unsaturated oxazolidinones:: Enantioselective synthesis of ent-pregabalin and baclofen

被引：32

作者：

Armstrong, Alan ^{[1
]}

Convine, Nicola J.

Popkin, Matthew E.

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

[2] GSK Tonbridge, Tonbridge TN11 9AN, Kent, England

来源：

SYNLETT | 2006年 / 10期

关键词：

conjugate addition; cyanide; samarium; oxazolidinone;

D O I：

10.1055/s-2006-941584

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of cyanide to chiral alpha, beta-unsaturated oxazolidinones catalyzed by samarium(III) isopropoxide proceeds with good diastereoselectivity. The addition products can be converted into the biologically active targets ent-pregabalin and baclofen.

引用

页码：1589 / 1591

页数：3

共 30 条

[1] Stereoselective cyanosilylation of α-sulfinylketimines or its covalently stabilized enamine tautomers.: Synthesis of enantiomerically pure α-sulfinylmethyl-α-amino nitriles
Acherki, H
Alvarez-Ibarra, C
Alfonso-de-Dios
Quiroga, ML
[J]. TETRAHEDRON, 2002, 58 (16) : 3217 - 3227
[2] ARMSTRONG A, 2005, COMPREHENSIVE ORGANI, V1, P287
[3] Michael addition of nitromethane to non-racemic chiral Cr(CO)3 complexes of ethyl cinnamate derivatives:: stereoselective synthesis of (R)-(-)-baclofen
Baldoli, C
Maiorana, S
Licandro, E
Perdicchia, D
Vandoni, B
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (09) : 2007 - 2014
[4] Enantioselective syntheses of (-)-(R)-rolipram, (-)-(R)-baclofen and other GABA analogues via rhodium-catalyzed conjugate addition of arylboronic acids
Becht, JM
Meyer, O
Helmchen, G
[J]. SYNTHESIS-STUTTGART, 2003, (18): : 2805 - 2810
[5] Val-Ala dipeptide isosteres by hydrocyanation of α′-amino α,β-unsaturated ketones -: Control of stereoselectivity by the N-protecting group
Benedetti, F
Berti, F
Garau, G
Martinuzzi, I
Norbedo, S
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (10) : 1973 - 1982
[6] Brenner M, 1999, HELV CHIM ACTA, V82, P2365, DOI 10.1002/(SICI)1522-2675(19991215)82:12<2365::AID-HLCA2365>3.0.CO
[7] 2-#
[8] An enantioselective synthesis of (S)-(+)-3-aminomethyl-5-methylhexanoic acid via asymmetric hydrogenation
Burk, MJ
de Koning, PD
Grote, TM
Hoekstra, MS
Hoge, G
Jennings, RA
Kissel, WS
Le, TV
Lennon, IC
Mulhern, TA
Ramsden, JA
Wade, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (14) : 5731 - 5734
[9] BURK MJ, 2001, Patent No. 0155090
[10] A generic approach for the catalytic reduction of nitriles
Caddick, S
Judd, DB
Lewis, AKD
Reich, MT
Williams, MRV
[J]. TETRAHEDRON, 2003, 59 (29) : 5417 - 5423

← 1 2 3 →