Enantioselective Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide,ACS Catalysis

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Enantioselective Conjugate Hydrocyanation of α,β-Unsaturated N-Acylpyrroles Catalyzed by Chiral Lithium(I) Phosphoryl Phenoxide
ACS Catalysis ( IF 11.3 ) Pub Date : 2017-09-01 00:00:00 , DOI: 10.1021/acscatal.7b02551
Manabu Hatano ₁ , Katsuya Yamakawa ₁ , Kazuaki Ishihara ₁

Affiliation

Enantioselective conjugate hydrocyanation of α,β-unsaturated N-acylpyrroles with the combined use of Me₃SiCN, LiCN, and HCN has been developed in the presence of a chiral lithium(I) phosphoryl phenoxide catalyst. This reaction is useful for a variety of N-acylpyrroles, including previously unreported substrates, such as heteroaryl and halogen-substituted N-cinnamoylpyrroles. A gram-scale reaction and subsequent transformations to a (R)-succinate, (S)-paraconic acid, and (R)-baclofen demonstrate an entry for the practical synthesis of optically active β-substituted γ-aminobutyric acids (GABA).

中文翻译：

手性磷酸锂（I）催化α，β-不饱和N-酰基吡咯的对映选择性共轭氢氰化

在手性锂（I）磷酰基苯酚催化剂的存在下，开发了结合使用Me ₃ SiCN，LiCN和HCN的α，β-不饱和N-酰基吡咯的对映选择性共轭氢氰化方法。该反应可用于多种N-酰基吡咯，包括先前未报告的底物，例如杂芳基和卤素取代的N-肉桂酰基吡咯。克级反应和随后的向（R）-琥珀酸酯，（S）-对锥酸和（R）-baclofen的转化证明了光学合成β-取代的γ-氨基丁酸（GABA）的实用合成方法。

更新日期：2017-09-04

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