Ring-Enlargement of in Situ Generated Cyclopropanones by the Reaction with Sulfonium Ylides: One-Pot Synthesis of Cyclobutanones

被引：4

作者：

Lange, Marvin ^{[1
]}

Werz, Daniel B. ^{[1
]}

机构：

[1] Albert Ludwigs Univ Freiburg, Inst Organ Chem, D-79104 Freiburg, Germany

来源：

ORGANIC LETTERS | 2024年 / 26卷 / 46期

关键词：

SULFUR YLIDES; DIASTEREOSELECTIVE SYNTHESIS; DERIVATIVES; EXPANSION; REARRANGEMENT; CYCLOADDITIONS; ANNULATION; KETENES; ETHERS; SALTS;

D O I：

10.1021/acs.orglett.4c03661

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this report, we describe a simple method for the synthesis of 2-aryl-2-vinyl-cyclobutanones through the reaction of in situ generated cyclopropanones and cinnamylsulfonium ylides, representing an example of a formal carbene insertion into these three-membered rings. The cyclobutanones thus obtained are ideal substrates for palladium-catalyzed coupling reactions upon enol triflate formation, thereby providing access to densely functionalized cyclobutenes. A mechanistic proposal for the ring-enlargement is presented based on experimental evidence.

引用

页码：9871 / 9876

页数：6

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