Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds.,Organic & Biomolecular Chemistry

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Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds.
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020-01-15 , DOI: 10.1039/c9ob02536g
Jiaxin Yang ₁ , Xiuxiu Li ₁ , Cai You ₁ , Shuailong Li ₁ , Yu-Qing Guan ₁ , Hui Lv ₁ , Xumu Zhang ₂

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A highly enantioselective hydrogenation of exocyclic α,β-unsaturated carbonyl compounds catalyzed by Rh/bisphosphine-thiourea (ZhaoPhos) has been developed, giving the corresponding α-chiral cyclic lactones, lactams and ketones with high yields and excellent enantioselectivities (up to 99% yield and 99% ee). Remarkably, the hydrogen bond between the substrate and the catalyst plays a critical role in this transformation. The synthetic utility of this protocol has been demonstrated by efficient synthesis of chiral 3-(4-fluorobenzyl)piperidine, a key chiral fragment of bioactive molecules.

中文翻译：

铑催化的环外α，β-不饱和羰基化合物的不对称氢化。

已开发出由Rh /双膦-硫脲（ZhaoPhos）催化的对环外α，β-不饱和羰基化合物的高度对映选择性氢化，可提供相应的α-手性环状内酯，内酰胺和酮，产率高且对映选择性极好（高达99％收率和99％ee）。显着地，底物和催化剂之间的氢键在该转变中起关键作用。该协议的合成用途已通过有效合成手性3-（4-氟苄基）哌啶（一种生物活性分子的关键手性片段）得到了证明。

更新日期：2020-02-13

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