β，β-二取代亚砜胺与乙烯基噻吩盐的正构[3 + 2]环化：3,3-二取代1-吡咯啉的不对称结构。

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-15 DOI:10.1021/acs.orglett.5c02008

Sheng-Cong Huang, and , Chong-Dao Lu*,

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引用次数: 0

摘要

在亚胺基α位置有一个季碳立体中心的五元内环亚胺，可以通过β，β-二取代亚胺与乙烯基噻吩盐的正[3 + 2]环形成立体选择性合成。去质子化的亚砜胺在乙烯基磺酸盐上发生亲核加成反应，随后发生分子内环化反应，生成具有高对映选择性的3,3-二取代1-吡啶衍生物。产物的立体化学性质受亚砜酰胺的几何构型和亚砜基的绝对构型的影响。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Formal [3 + 2] Annulation of β,β-Disubstituted Enesulfinamides with Vinyl Thianthrenium Salt: Asymmetric Construction of 3,3-Disubstituted 1-Pyrrolines

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Formal [3 + 2] Annulation of β,β-Disubstituted Enesulfinamides with Vinyl Thianthrenium Salt: Asymmetric Construction of 3,3-Disubstituted 1-Pyrrolines

Five-membered endocyclic imines featuring a quaternary carbon stereocenter at the α position of the imino group can be stereoselectively synthesized through the formal [3 + 2] annulation of β,β-disubstituted enesulfinamides with vinyl thianthrenium salt. The deprotonated enesulfinamides undergo a nucleophilic addition to the vinyl sulfonium salt, which is followed by intramolecular cyclization, leading to the production of 3,3-disubstituted 1-pyrroline derivatives with high enantioselectivity. The stereochemistry of the resulting products is influenced by both the geometric configuration of the enesulfinamides and the absolute configuration of their sulfinyl group.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.