One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives

被引：0

作者：

Janssens, Julien ^{[1
]}

De Roose, Madeline ^{[1
]}

Jacquemin, Alexis ^{[1
]}

Vanhosmael, Thomas ^{[1
]}

Delbrassinne, Arnaud ^{[1
]}

Collard, Laurent ^{[1
]}

Robiette, Raphael ^{[1
]}

机构：

[1] Catholic Univ Louvain, Inst Condensed Matter & Nanosci, B-1348 Louvain La Neuve, Belgium

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 10期

关键词：

MEDIATED ASYMMETRIC EPOXIDATIONS; CATALYTIC HOMOLOGATION; ALKENE HOMOLOGATION; METATHESIS; ETHYLENE; SCOPE; VINYLCYCLOPROPANE; MECHANISM; ESTERS;

D O I：

10.1021/acs.joc.4c00057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-carbon homologation of Knoevenagel adducts enabling the insertion of a CHAr fragment is reported. The strategy involves a sulfur ylide mediated cyclopropanation followed by the rearrangement of cyclopropanes and enables the synthesis of a series of benzhydryl derivatives. Mechanistic studies reveal that the cyclopropane rearrangement involves a Lewis acid catalyzed ring-opening followed by the 1,2-migration of an aryl group. The possibility of controlling the absolute stereochemistry of the generated stereogenic allylic carbon center using a chiral sulfonium ylide is demonstrated.

引用

页码：7270 / 7274

页数：5

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