(4+3) Cycloaddition Reactions of Nitrogen-Stabilized Oxyallyl Cations

• Published in: Chemistry : a European journal Vol. 17; no. 14; pp. 3812 - 3822
• Main Authors: Lohse, Andrew G., Hsung, Richard P.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 28.03.2011; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: Allyl Compounds - chemistry; Cations; Cations - chemistry; Chemistry; Cyclization; Cycloaddition; Halogens; heterocycles; Molecular Structure; Nitrogen; Nitrogen - chemistry; oxyallyl cations; Prominences; regioselectivity; Stereoisomerism; Sulfur
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201100260

The use of heteroatom‐substituted oxyallyl cations in (4+3) cycloadditions has had a tremendous impact on the development of cycloaddition chemistry. Extensive efforts have been exerted toward investigating the effect of oxygen, sulfur, and halogen substituents on the reactivity of oxyallyl cations. Most recently, the use of nitrogen‐stabilized oxyallyl cations has gained prominence in the area of (4+3) cycloadditions. The following article will provide an overview of this concept utilizing nitrogen‐stabilized oxyallyl cations. A new leaf for (4+3) cycloadditions! Heteroatom‐substituted (4+3) cycloadditions have had a tremendous impact on the development of cycloaddition chemistry. Extensive efforts have been exerted toward investigating the effect of oxygen‐, sulfur‐, and halogen‐substituents on the reactivity of oxyallyl cations. Most recently, the use of nitrogen‐stabilized oxyallyl cations has gained prominence in the area of (4+3) cycloadditions.