Enantioselective synthesis of beta-substituted butyric acid derivatives via orthoester Claisen rearrangement of enzymatically resolved allylic alcohols: application to the synthesis of (R)-(-)-baclofen

被引：54

作者：

Brenna, E

Caraccia, N

Fuganti, C

Fuganti, D

Grasselli, P

机构：

[1] Dip. Chimica del Politecnico, Ctro. CNR Chim. Sostanze O., I-20131 Milano

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(97)00538-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A three step synthesis of (R)-(-)-baclofen is described. The key step is the orthoester Claisen rearrangement of enantiopure allylic alcohol (S,E)-(-).la, affording gamma,delta-unsaturated ester (S,E)-(+)-6 with high stereoselectivity. This latter derivative is converted into (R)-(-)-baclofen through a high yield one-pot reaction. (C) 1997 Elsevier Science Ltd.

引用

页码：3801 / 3805

页数：5

共 13 条

[1] Optical resolution of baclofen via diastereomeric salt pair formation between 3-(p-chlorophenyl)glutaramic acid and (S)-(-)-alpha-phenylethylamine
Caira, MR
Clauss, R
Nassimbeni, LR
Scott, JL
Wildervanck, AF
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (04): : 763 - 768
[2] QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS
CHEN, CS
FUJIMOTO, Y
GIRDAUKAS, G
SIH, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) : 7294 - 7299
[3] BAKERS YEAST-MEDIATED SYNTHESIS OF (R)-AMINOGLUTETHIMIDE
FOGLIATO, G
FRONZA, G
FUGANTI, C
GRASSELLI, P
SERVI, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) : 5693 - 5695
[4] BAKERS-YEAST MEDIATED PREPARATION OF ESTERS OF (R)-ETHYL AND (S)-ETHYL 2-FORMYL-3-HYDROXY-2-METHYLPROPIONATE
FRONZA, G
FUGANTI, C
GRASSELLI, P
MALPEZZI, L
MELE, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3487 - 3489
[5] Microbially-aided preparation of (S)-2-methoxycyclohexanone key intermediate in the synthesis of sanfetrinem
Fuganti, C
Grasselli, P
Mendozza, M
Servi, S
Zucchi, G
[J]. TETRAHEDRON, 1997, 53 (07) : 2617 - 2624
[6] FUGANTI C, 1984, J CHEM RES M, P976
[7] BACLOFEN IN TREATMENT OF SPASTICITY
HUDGSON, P
WEIGHTMAN, D
[J]. BMJ-BRITISH MEDICAL JOURNAL, 1971, 4 (5778): : 15 - +
[8] A SIMPLE STEREOSELECTIVE VERSION OF CLAISEN REARRANGEMENT LEADING TO TRANS-TRISUBSTITUTED OLEFINIC BONDS . SYNTHESIS OF SQUALENE
JOHNSON, WS
WERTHEMANN, L
BARTLETT, WR
BROCKSOM, TJ
LI, TT
FAULKNER, DJ
PETERSEN, MR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (03) : 741 - +
[9] ENANTIOSELECTIVE PREPARATION OF BETA-ALKYL-GAMMA-BUTYROLACTONES FROM FUNCTIONALIZED KETENE DITHIOACETALS
KOCH, SSC
CHAMBERLIN, AR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (10) : 2725 - 2737
[10] A chemoenzymatic strategy for the synthesis of enantiopure (R)-(-)-baclofen
Mazzini, C
Lebreton, J
Alphand, V
Furstoss, R
[J]. TETRAHEDRON LETTERS, 1997, 38 (07) : 1195 - 1196

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