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Synlett 2015; 26(02): 183-186
DOI: 10.1055/s-0034-1379428
DOI: 10.1055/s-0034-1379428
letter
Methylprenyl and Prenyl Protection for Sulfonamides
Further Information
Publication History
Received: 12 September 2014
Accepted after revision: 18 October 2014
Publication Date:
14 November 2014 (online)
Dedicated to Dr. Valerjans Kauss on the occasion of his 60th birthday
Abstract
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.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379428. Included are synthetic procedures for compounds 1a–m, 2a–j, 3, 9, 10, 12 and 13–15, their spectroscopic characterisation as well as NMR spectra of compounds 1a–g, 1i–j and 13–15.
- Supporting Information
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References and Notes
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