Synthesis of Chiral 2-Hydroxy-1-methylpropanoates by Rhodium-Catalyzed Stereoselective Hydrogenation of α-(Hydroxymethyl)-acrylate Derivatives

被引：23

作者：

Holz, Jens ^{[1
]}

Schaeffner, Benjamin ^{[1
]}

Zayas, Odalys ^{[2
]}

Spannenberg, Anke ^{[1
]}

Boerner, Armin ^{[1
,2
]}

机构：

[1] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany

[2] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

asymmetric catalysis; hydrogenation; kinetic resolution; phospholanes; rhodium;

D O I：

10.1002/adsc.200800525

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of chiral 3-hydroxy-2-methyl propanoic acid esters (e.g., "Roche ester" 3a) based on the rhodium-catalyzed stereoselective hydrogenation of Baylis-Hillman reaction products was investigated. Full conversions and enantioselectivities of up to 99% at a substrate/catalyst ratio of up to 500/1 were achieved by application of bisphospholaries of the catASium M series as ancillary ligands. An interesting kinetic resolution was observed by the diastereoselective hydroxy-directed hydrogenation of related racemic P-branched precursors affording mainly anti-isomers with up to 96%ee.

引用

页码：2533 / 2543

页数：11

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