期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 -, 期 -, 页码 -出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202217064
关键词
Aziridines; Bicyclo[1; 1; 0]Butanes; Epoxides; Spiro Compounds; Strained Molecules
The development of preparative methods for the synthesis of four-membered carbocycles is important for their utility in medicinal chemistry. A new methodology for producing spirocyclic epoxides and aziridines with a cyclobutane motif was developed. The reaction is efficient and can tolerate a broad variety of substrates. The products can be used as modular building blocks for introducing three-dimensional structures into target molecules.
The development of preparative methods for the synthesis of four-membered carbocycles is gaining increasing importance due to the widespread utility of cyclic compounds in medicinal chemistry. Herein, we report the development of a new methodology for the production of spirocyclic epoxides and aziridines containing a cyclobutane motif. In a two-step one-pot process, a bicyclo[1.1.0]butyl sulfoxide is lithiated and added to a ketone, aldehyde or imine, and the resulting intermediate is cross-coupled with an aryl triflate through C-C sigma-bond alkoxy- or aminopalladation with concomitant epoxide or aziridine formation. After careful optimization, a remarkably efficient reaction was conceived that tolerated a broad variety of both aromatic and aliphatic substrates. Lastly, through several high yielding ring-opening reactions, we demonstrated the excellent applicability of the products as modular building blocks for the introduction of three-dimensional structures into target molecules.
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