Lewis酸促进环丙烯级联反应：一种立体选择性合成环醚和草螺内酯的统一方法

IF 4.3 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chemical Communications Pub Date : 2025-05-28 DOI:10.1039/d5cc00925a

Santosh J. Gharpure, Krishna Suraj Gupta, Rakhi Yadav

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引用次数: 0

摘要

Lewis酸促进ω-羟基环丙烯的5/6-外三角氢烷氧基化/还原级联反应，Lewis酸促进-羟基环丙烯的5/6-外三角氢烷氧基化/还原级联反应，使THF/THP衍生物具有快速的立体选择性。单酯取代-羟基环丙烯在催化Bi(OTf)3处理下得到[5,5]/[6,5]草螺环内酯。这种统一的策略依赖于从-羟基环丙烯前体生成瞬态供体-受体（D-A）环丙烷。这种方法允许在“一锅”过程中连续添加两种亲核试剂来合成THP衍生物。该方法在（±）-果子狸同系物的立体选择性合成中得到了应用。

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Lewis Acid-Promoted Cascade Reactions of Cyclopropenes: A Unified Approach to Stereoselective Synthesis of Cyclic Ethers and Oxaspirolactones

Lewis acid promoted 5/6-exo trig hydroalkoxylation/reduction cascade of ω-hydroxy cyclopropenes gave eLewis acid promoted 5/6-exo trig hydroalkoxylation/reduction cascade of -hydroxy cyclopropenes gave expeditious, stereoselective access to THF/THP derivatives. Monoester substituted -hydroxy cyclopropenes on treatment with catalytic Bi(OTf)3 lead to [5,5]/[6,5] oxaspirocyclic lactones. This unified strategy relies on generation of transient donor-acceptor (D-A) cyclopropanes from -hydroxy cyclopropene precursors. This approach allows for the sequential addition of two nucleophiles in ‘one pot’ process for the synthesis of THP derivatives. The utility of this methodology is demonstrated in the stereoselective synthesis of homologue of (±)-civet.

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来源期刊

Chemical Communications 化学-化学综合

CiteScore

8.60

自引率

4.10%

发文量

2705

审稿时长

1.4 months

期刊介绍： ChemComm (Chemical Communications) is renowned as the fastest publisher of articles providing information on new avenues of research, drawn from all the world''s major areas of chemical research.