Catalytic Asymmetric Synthesis of Chiral Oxaspirolactones and Tetrahydropyrans via Ammonium-Catalyzed Reactions of Vinyl Ketones and Nitroalcohols.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-25 DOI:10.1021/acs.orglett.5c03634

Xi-Ming Ma,Yong-Chao Ming,Xue-Jiao Lv,Yan-Kai Liu

引用次数: 0

Abstract

Chiral oxaspirolactones and tetrahydropyrans are important motifs found in various bioactive molecules and pharmaceuticals. Herein, we report a highly enantioselective Michael addition-initiated reaction sequence between vinyl ketones and nitroalcohols, catalyzed by a novel chiral ammonium phase-transfer catalyst to afford the key cyclic hemiketals. These hemiketals serve as versatile intermediates for constructing oxaspirolactones and 2,5-disubstituted tetrahydropyrans with high enantioselectivity and excellent diastereoselectivity. This method features a broad substrate scope and provides access to various structurally diverse products.

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乙烯基酮和硝基醇氨催化不对称合成手性奥斯匹内酯和四氢吡喃。

手性奥斯匹内酯和四氢吡喃是各种生物活性分子和药物中的重要基序。本文报道了一种新的手性铵相转移催化剂催化乙烯基酮和硝基醇之间的高对映选择性迈克尔加成反应序列，以获得关键的环半酮。这些半酮类化合物可作为多用途的中间体，用于构建草螺内酯和2,5-二取代四氢吡喃，具有高对映选择性和优异的非对映选择性。该方法具有广泛的衬底范围，并提供了各种结构多样的产品的访问。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.