Phosphine-Catalyzed Asymmetric Dearomative Annulation of 4-Nitroisoxazoles with Allenoates: Construction of Isoxazoline-Fused Bicyclo[3.3.0]octenes

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-13 DOI:10.1021/acs.orglett.5c01958

Huamin Wang*, Hong-Ding Xie, Jun-Long Ding, Yanjun Xie, Ying-Wu Lin* and Junliang Zhang*,

引用次数: 0

Abstract

An intermolecular phosphine-catalyzed dearomatization reaction of 4-nitroisoxazoles with allenoates was realized through one-pot sequential [3 + 2]/[3 + 2] annulation. Various isoxazoline-fused bicyclo[3.3.0]octene derivatives were successfully synthesized in good to excellent yields (up to 98%). Under catalysis with SadPhos P7, enantioselective dearomative cyclization occurred, initiating the subsequent [3 + 2] cycloaddition process to afford valuable optically active cyclopentane-fused polycyclic scaffolds bearing a quaternary carbon stereocenter in 58–98% yields with 70–97% ee. The synthetic utility of this protocol was demonstrated by the gram-scale reaction and versatile transformations of the product.

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膦催化4-硝基异恶唑与烯丙酸酯的不对称脱芳环化：异恶唑-融合双环[3.3.0]辛烯的构建

通过一锅连续[3 + 2]/[3 + 2]环化，实现了分子间膦催化4-硝基异恶唑与烯丙酸酯的脱芳反应。成功合成了多种异恶唑-融合的双环[3.3.0]辛烯衍生物，收率可达98%。在SadPhos P7的催化下，发生了对映选择性脱芳环化反应，引发了随后的[3 + 2]环加成过程，得到了具有光学活性的含季碳立体中心的环戊烷-融合多环支架，产率为58-98%，ee为70-97%。克级反应和产物的多用途转化证明了该方案的合成效用。

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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.