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开发一种改进的体系,以在酮与烯丙酰胺的线性选择性铜催化还原偶联反应中提供更好的非对映体控制。

Development of a Modified System to Provide Improved Diastereocontrol in the Linear-Selective Cu-Catalyzed Reductive Coupling of Ketones and Allenamides.

作者信息

Ho Dang Binh, Gargaro Samantha, Klake Raphael K, Sieber Joshua D

机构信息

Department of Chemistry, Virginia Commonwealth University, 1001 West Main Street, Richmond, Virginia 23284-3208, United States.

Medicines for All Institute, Virginia Commonwealth University, 737 North Fifth Street, Richmond, Virginia 23219, United States.

出版信息

J Org Chem. 2022 Feb 18;87(4):2142-2153. doi: 10.1021/acs.joc.1c02062. Epub 2021 Nov 22.

Abstract

Chiral γ-lactones are prevalent organic architectures found in a large array of natural products. In this work, we disclose the development of a modified catalytic system utilizing a commercially available Cu-phosphite catalyst for the diastereoselective reductive coupling of chiral allenamides and ketones to afford chiral γ-lactone precursors in 80:20 to 99:1 dr.

摘要

手性γ-内酯是大量天然产物中普遍存在的有机结构。在本研究中,我们报道了一种改进的催化体系的开发,该体系利用市售的亚磷酸铜催化剂对手性烯丙酰胺和酮进行非对映选择性还原偶联,以80:20至99:1的非对映体比例得到手性γ-内酯前体。

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