β，γ-不饱和酮肟的氧磺酰基化：异恶唑啉的对映选择性合成

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-17 DOI:10.1021/acs.orglett.6c03683

Akshaya Kumar Sahu,Pazhamalai Anbarasan

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引用次数: 0

摘要

摘要提出了一种手性路易斯碱催化β，γ-不饱和肟双功能化的对映选择性氧亚砜化策略。高对映选择性是通过引入邻苯二胺衍生的苄基亚砜基试剂，而不是传统的大体积或邻取代噻吩衍生物，在HFIP中使用刘易斯碱催化剂，在没有酸添加剂的情况下实现的。该反应显示出广泛的底物范围，并通过形成C-O和C-S键，以高收率和优异的对映体比（高达97:3 er）构建了各种硫系异恶唑啉。

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Catalytic Oxysulfenylation of β,γ-Unsaturated Ketoximes: An Enantioselective Synthesis of Isoxazolines

Abstract We present a chiral Lewis base-catalyzed enantioselective oxysulfenylation strategy for the difunctionalization of β,γ-unsaturated oximes. High enantioselectivity was achieved through the introduction of phthalimide-derived benzylsulfenyl reagents, instead of traditional bulky or ortho-substituted thiophenol derivatives, with Lewis base catalysts in HFIP in the absence of an acid additive. The reaction demonstrates a wide substrate scope, and various sulfur-tethered isoxazolines were constructed with high yields and excellent enantiomeric ratios (up to 97:3 er) via the formation of C–O and C–S bonds.

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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.