在有机催化条件下对映体富集的β-硅基硝基烷烃的无溶剂合成。
Solvent-free synthesis of enantioenriched β-silyl nitroalkanes under organocatalytic conditions.
作者信息
Dubey Akhil K, Chowdhury Raghunath
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. 2021 Oct 27;17:2642-2649. doi: 10.3762/bjoc.17.177. eCollection 2021.
Abstract
An enantioselective 1,4-conjugate addition of nitromethane to β-silyl α,β-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silyl nitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.
摘要
已经开发了一种由双功能方酰胺催化剂催化的硝基甲烷对β-硅基α,β-不饱和羰基化合物的对映选择性1,4-共轭加成反应。该方法在无溶剂条件下于室温下能以良好至优异的产率（高达92%）和对映选择性（高达97.5% ee）提供β-硅基硝基烷烃的两种对映体。对照实验表明，在优化的反应条件下，烯酮中β-硅基的存在对于高反应活性至关重要。
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