Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position†,Chemical Science

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Rhodium-catalyzed asymmetric hydrogenation of β-cyanocinnamic esters with the assistance of a single hydrogen bond in a precise position†
Chemical Science ( IF 7.6 ) Pub Date : 2018-01-04 00:00:00 , DOI: 10.1039/c7sc04639a
Xiuxiu Li ₁ , Cai You ₁ , Yusheng Yang ₁ , Yuhong Yang ₂ , Pan Li ₁ , Guoxian Gu ₂ , Lung Wa Chung ₂ , Hui Lv _{1,

3} , Xumu Zhang _{1,

2}

Affiliation

With the assistance of hydrogen bonds, the first asymmetric hydrogenation of β-cyanocinnamic esters is developed, affording chiral β-cyano esters with excellent enantioselectivities (up to 99% ee). This novel methodology provides an efficient and concise synthetic route to chiral GABA-derivatives such as (S)-Pregabalin, (R)-Phenibut, (R)-Baclofen. Interestingly, in this system, the catalyst with a single H-bond donor performs better than that with double H-bond donors, which is a novel discovery in the metalorganocatalysis area.

中文翻译：

在精确位置的单个氢键的帮助下，铑催化的β-氰基肉桂酸酯不对称氢化†

在氢键的帮助下，首次开发了 β-氰基肉桂酸酯的不对称氢化，提供了具有优异对映选择性（高达 99% ee）的手性 β-氰基酯。这种新的方法为手性 GABA 衍生物（如 ( S )-普瑞巴林、( R )-Phenibut、( R )-巴氯芬）提供了一种有效且简洁的合成途径。有趣的是，在该体系中，单氢键供体催化剂的性能优于双氢键供体，这是金属有机催化领域的一个新发现。

更新日期：2018-01-04

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