Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl-Gold Promoted Intermolecular Ynamide Addition to Aldehydes,Angewandte Chemie International Edition

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Asymmetric Hydrative Aldol Reaction (HAR) via Vinyl-Gold Promoted Intermolecular Ynamide Addition to Aldehydes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2023-06-05 , DOI: 10.1002/anie.202305810
Teng Yuan ₁ , Kelton Radefeld ₁ , Chuan Shan ₁ , Carter Wegner ₁ , Erin Nichols ₁ , Xiaohan Ye ₁ , Qi Tang ₁ , Lukasz Wojtas ₁ , Xiaodong Shi ₁

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The application of Fe(acac)₃ as a cocatalyst prevents vinyl gold protodeauration, allowing for its nucleophilic addition to aldehydes. Hence, the intermolecular vinyl gold-promoted asymmetric hydrative aldol reaction (HAR) of ynamides and aldehydes was shown possible and is herein presented. The reaction leads to β-hydroxy amides with high yields (up to 95 %) and stereoselectivity (up to >20 : 1 d.r, 99 % ee) under mild conditions (base-free, 40 °C).

中文翻译：

通过乙烯基-金促进分子间酰胺加成至醛的不对称水合羟醛反应 (HAR)

Fe(acac) ₃作为助催化剂的应用可防止乙烯基金原脱气，从而使其能够与醛发生亲核加成。因此，分子间乙烯基金促进的炔酰胺和醛的不对称水合羟醛反应（HAR）被证明是可能的，并在本文中提出。该反应在温和条件（无碱，40 °C）下产生高产率（高达 95 %）和立体选择性（高达 >20 : 1 dr，99 % ee）的 β-羟基酰胺。

更新日期：2023-06-05

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