Methylprenyl and Prenyl Protection for Sulfonamides
Synlett
2015
Anna Nikitjuka,
Aleksandra Nekrasova,
Aigars Jirgensons
2-Methylprenyl (MePre) is an efficient protection for sulfonamides. The acidic cleavage of this group leads to volatile by-products and the product can be obtained in high purity without additional purification. MePre group is resistant to Pd/C-catalysed hydrogenolysis at 1 atm, Suzuki–Miyaura reaction, Ni(0) catalysis conditions and oxidising reagents such as NIS and DDQ. The prenyl (Pre) group can also be used to protect sulfonamides in certain cases; however, the substrate scope is limited due to the side product formation.
Keywords
sulfonamides - protecting groups - allylation - cations - cleavage
DOI
10.1055/s-0034-1379428
Hyperlink
https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0034-1379428
Nikitjuka, A., Nekrasova, A., Jirgensons, A. Methylprenyl and Prenyl Protection for Sulfonamides. Synlett, 2015, Vol.26, Iss.2, pp.183-186. ISSN 0936-5214. Available from: doi:10.1055/s-0034-1379428
Publication language
English (en)