伯胺催化的吡唑啉-5-酮与α,β-不饱和酮的对映选择性1,4-迈克尔加成反应。
Primary amine-catalyzed enantioselective 1,4-Michael addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones.
作者信息
Goyal Pooja, Dubey Akhil K, Chowdhury Raghunath, Wadawale Amey
机构信息
Bio-Organic Division, Bhabha Atomic Research Centre, Trombay, Mumbai 400085, India.
Homi Bhabha National Institute, Anushaktinagar, Mumbai 400094, India.
出版信息
Beilstein J Org Chem. 2024 Jul 9;20:1518-1526. doi: 10.3762/bjoc.20.136. eCollection 2024.
The enantioselective 1,4-addition reaction of pyrazolin-5-ones to α,β-unsaturated ketones catalyzed by a cinchona alkaloid-derived primary amine-Brønsted acid composite is reported. Both enantiomers of the anticipated pyrazole derivatives were obtained in good to excellent yields (up to 97%) and high enantioselectivities (up to 98.5% ee) under mild reaction conditions. In addition, this protocol was further expanded to synthesize highly enantioenriched hybrid molecules bearing biologically relevant heterocycles.
报道了一种由金鸡纳生物碱衍生的伯胺-布朗斯特酸复合物催化的吡唑啉-5-酮与α,β-不饱和酮的对映选择性1,4-加成反应。在温和的反应条件下，预期的吡唑衍生物的两种对映体均以良好至优异的产率（高达97%）和高对映选择性（高达98.5% ee）得到。此外，该方法进一步扩展用于合成带有具有生物学相关性的杂环的高度对映体富集的杂化分子。
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