Enantioselective Organocatalytic Syntheses and Ring-Expansions of Cyclobutane Derivatives

被引:10
作者
Barday, Manuel [1 ]
Bouillac, Pierre [1 ]
Coquerel, Yoann [1 ]
Amatore, Muriel [1 ]
Constantieux, Thierry [1 ]
Rodriguez, Jean [1 ]
机构
[1] Aix Marseille Univ, CNRS, Cent Marseille, iSm2, Marseille, France
关键词
Medium-ring compounds; Organocatalysis; Ring expansion; Small ring systems; Strained molecules; INTERMOLECULAR 2+2 PHOTOCYCLOADDITION; SEMI-PINACOL REARRANGEMENT; BRONSTED ACID; CYCLOADDITION REACTIONS; NATURAL-PRODUCTS; CYCLOBUTENONES; BOND; ACTIVATION; CATALYSIS; FLUORINATION;
D O I
10.1002/ejoc.202100405
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The progress in enantioselective organocatalysis have enabled efficient and highly stereoselective syntheses of cyclobutane derivatives, through (2+2) annulation reactions, overcoming the geometrical constraints inherent to these small cyclic molecules. More importantly, and taking advantage of their strain-releasing fragmentation, some cyclobutane derivatives, especially cyclobutanones and cyclobutenones, can now be regarded as versatile four-carbon atoms units amenable to the enantioselective construction of larger rings by (4+n) annulation reactions to produce, five-, six-, seven- and eight-membered cyclic products. These recent developments concerning the enantioselective synthetic chemistry of cyclobutane derivatives under organocatalytic conditions are reviewed herein.
引用
收藏
页码:3023 / 3034
页数:12
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