Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 14, Pages 1991-2007Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1690869
Keywords
Prins; annulations; cyclizations; natural products; oxa-cycles; azacycles; alkynes
Categories
Funding
- American Chemical Society Petroleum Research Fund [58776-NDI]
- National Science Foundation [CHE-1900050]
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This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization- processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing- saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericyclic reactions, including [4+2] cycloadditions and Nazarov electrocyclizations, to rapidly construct complex small molecules. Finally, examples of the use of alkynyl Prins and alkynyl aza-Prins reactions in the synthesis of natural products are described. The review covers the literature through the end of 2019.
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