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通过对亚芳基异恶唑-5-酮的共轭加成和钼（羰基）介导的还原级联反应制备β-烷基化γ-官能化酮

Access to β-Alkylated γ-Functionalized Ketones via Conjugate Additions to Arylideneisoxazol-5-ones and Mo(CO)-Mediated Reductive Cascade Reactions.

作者信息

Macchia Antonio, Summa Francesco F, Monaco Guglielmo, Eitzinger Andreas, Ofial Armin R, Di Mola Antonia, Massa Antonio

机构信息

Dipartimento di Chimica e Biologia "A. Zambelli", Università degli studi di Salerno, Via Giovanni Paolo II, 84084 Fisciano, Salerno, Italy.

Department Chemie, Ludwig-Maximilians-Universität Munchen, 81377 Munchen, Germany.

出版信息

ACS Omega. 2022 Mar 4;7(10):8808-8818. doi: 10.1021/acsomega.1c07081. eCollection 2022 Mar 15.

DOI:10.1021/acsomega.1c07081
PMID:35309475
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8928520/
Abstract

1,4-Conjugate addition of ((chloromethyl)sulfonyl)benzenes to arylideneisoxazol-5-ones, followed by one-pot, N-selective trapping in the presence of electrophiles, was investigated. This strategy led to the synthesis of new, stable N-protected isoxazol-5-ones in good yields and high diastereolectivity. The study of the reactivity of obtained products in the presence of the Mo(CO)/HO system allowed the development of a cascade reaction leading to novel methyl ketones in high yields and unchanged dr bearing an uncommon chloromethinearylsulfonyl end group.

摘要

研究了((氯甲基)磺酰基)苯与亚芳基异恶唑-5-酮的1,4-共轭加成反应，随后在亲电试剂存在下进行一锅法N-选择性捕获。该策略以良好的产率和高非对映选择性合成了新型稳定的N-保护异恶唑-5-酮。对所得产物在Mo(CO)/HO体系存在下的反应性研究使得开发出一种级联反应，该反应能以高产率和不变的非对映选择性得到带有不常见氯甲基芳基磺酰基端基的新型甲基酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/f0450a71250d/ao1c07081_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/65b3a676a526/ao1c07081_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/299df68bc2ba/ao1c07081_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/fc6c7ff2a028/ao1c07081_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/80edd967c198/ao1c07081_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/f0450a71250d/ao1c07081_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/65b3a676a526/ao1c07081_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/299df68bc2ba/ao1c07081_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/fc6c7ff2a028/ao1c07081_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/80edd967c198/ao1c07081_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7337/8928520/f0450a71250d/ao1c07081_0006.jpg

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