Studies Toward Improved Enantiocontrol in the Asymmetric Cu-Catalyzed Reductive Coupling of Ketones and Allenamides: 1,2-Aminoalcohol Synthesis
Studies Toward Improved Enantiocontrol in the Asymmetric Cu-Catalyzed Reductive Coupling of Ketones and Allenamides: 1,2-Aminoalcohol Synthesis
复制标题
酮和烯丙酰胺不对称铜催化还原偶联中改进对映体控制的研究：1,2-氨基醇合成
DOI：
10.1021/acs.orglett.3c00157
复制
发表时间：
2023
期刊：
影响因子：
5.2
通讯作者：
Sieber, Joshua D.
中科院分区：
文献类型：
--
作者：
Collins, Stephen;Sieber, Joshua D.
本文报道了一种改进的铜催化酮和烯酰胺的对映选择性还原偶联系统的发展，通过优化烯酰胺以避免循环重排。对多种酮具有较高的对映选择性。使用本文所述的非环烯酰胺选择性地生成抗非对映体，与先前显示有利于合成形式的环烯酰胺相反。还提出了这种非对映选择性变化的基本原理。
Herein, we report the development of an improved system for the Cu-catalyzed enantioselective reductive coupling of ketones and allenamides through the optimization of the allenamide to avoid an on-cycle rearrangement. High enantioselectivities could be obtained for a variety of ketones. Use of the acyclic allenamides described herein selectively generatedanti-diastereomers in contrast to cyclic allenamides that were previously shown to favor thesyn-form. A rationale for this change in diastereoselectivity is also presented.