通过热促进烷基吡啶盐与亚磺酰亚胺的脱氨基加成反应制备α-手性胺
α-Chiral Amines via Thermally Promoted Deaminative Addition of Alkylpyridinium Salts to Sulfinimines.
作者信息
Baker Kristen M, Tallon Amanda, Loach Richard P, Bercher Olivia P, Perry Matthew A, Watson Mary P
机构信息
Department of Chemistry & Biochemistry, University of Delaware, Newark, Delaware 19716, United States.
Pfizer Medicinal Sciences, Eastern Point Road, Groton, Connecticut 06340, United States.
出版信息
Org Lett. 2021 Oct 15;23(20):7735-7739. doi: 10.1021/acs.orglett.1c02708. Epub 2021 Sep 27.
Abstract
A deaminative reaction of Katritzky alkylpyridinium salts and sulfinimines has been developed to deliver enantiopure α-chiral amines. The success of this method relied on the discovery of a thermally promoted deamination via single-electron transfer of an anion-π complex of the alkylpyridinium cation with potassium carbonate. This method boasts excellent diastereoselectivity over the α-stereocenter as well as broad functional group and heterocycle tolerance.
摘要
已开发出一种卡氏吡啶鎓盐与亚磺酰亚胺的脱氨基反应，用于制备对映体纯的α-手性胺。该方法的成功依赖于通过碳酸钾与烷基吡啶鎓阳离子的阴离子-π络合物的单电子转移实现热促进脱氨基反应的发现。该方法在α-立体中心具有出色的非对映选择性，并且对官能团和杂环具有广泛的耐受性。
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