Regio- and Diastereoselective 1,3-Dipolar Cycloaddition between Perfluoro-2-methyl-2-pentene and Nitrones: A Facile Approach to Partially-Fluorinated Isoxazolidines

Moon, Mi-Eun; Park, Joo Yeon; Jeong, Eun-Ha; Vajpayee, Vaishali; Kim, Hyunuk; Chi, Ki‐Whan

doi:10.5012/bkcs.2010.31.6.1515

Cited by 6 publications

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Carboamination and Alkylative Cyclization withCNBond Formation in Stereoselective Syntheses

Ghorai

Halder

Samanta

2013

Stereoselective Synthesis of Drugs and Natural Products

View full text Add to dashboard Cite

The carboamination reaction can be considered an important and fascinating tool for atom‐economic and convergent construction toward the functionalized N ‐containing cyclic compounds. Because the aza‐cycle is frequently found in almost all members of the alkaloid family with immense synthetic and pharmacological activities, the formation of this ring system is a highly demanding task for synthetic organic chemists. As a result, several rational techniques have been developed including intramolecular S N 2 reactions, reductive amination reactions, conjugate addition reactions, metal‐ and acid‐catalyzed cyclizations, and ring‐closing olefin metathesis reactions. Despite the many available routes, the carboamination strategy could be one of the best techniques considering stereoselectivity and the step economic path toward the formation of ring compounds in an elegant way.Alkylative cyclization with CN bond formation ( N ‐alkylation) is one of the most important methods in organic synthesis for the construction of aza‐cycles. Many well‐known name reactions (e.g., aza‐Diels‐Alder, aza‐Michael, aza‐Mannich, aza‐Henry reactions, etc.), which are generally being employed in the intramolecular CN bond formation step, can be treated as CN alkylative cyclization. It is an extremely powerful method for the stereoselective synthesis of N ‐heterocycles like aziridines, azetidines, lactams, pyrrolidines, piperidines, amino sugars, and many more, which are the basic structural units present in many natural products and biologically active compounds.

show abstract