通过手性 N-磷酰亚胺的 Brønsted 酸催化不对称氮杂-Baylis-Hillman 反应合成非对映过剩的 α-氨甲基烯胺酮。
Synthesis of Diastereoenriched α-Aminomethyl Enaminones via a Brønsted Acid-Catalyzed Asymmetric aza-Baylis-Hillman Reaction of Chiral N-Phosphonyl Imines.
机构信息
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas, 79409-1061, USA.
School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou, 221116, China.
出版信息
Chem Asian J. 2020 Apr 1;15(7):1125-1131. doi: 10.1002/asia.201901734. Epub 2020 Mar 4.
An effective chiral GAP methodology for preparing α-aminomethyl enaminones through a (R)-CSA-catalyzed asymmetric aza-Baylis-Hillman reaction is reported. Excellent yields and high diastereoselectivity could be obtained under mild conditions and convenient GAP techniques. The confirmations of the absolute configuration of N-phosphonyl imine and chiral enaminone by X-ray diffraction provides an explicit explanation of the chirality mechanism for GAP chemistry.
本文报道了一种有效的手性 GAP 方法，通过（R）-CSA 催化的不对称氮杂-Baylis-Hillman 反应制备α-氨甲基烯胺酮。在温和的条件下和方便的 GAP 技术下，可以获得优异的产率和高的非对映选择性。通过 X 射线衍射对 N-膦酰亚胺和手性烯胺酮的绝对构型的确定，为 GAP 化学的手性机制提供了明确的解释。
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