Synlett 2015; 26(02): 183-186
DOI: 10.1055/s-0034-1379428
letter
© Georg Thieme Verlag Stuttgart · New York

Methylprenyl and Prenyl Protection for Sulfonamides

Anna Nikitjuka, Aleksandra Nekrasova, Aigars Jirgensons*
  • Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga 1006, Latvia   Fax: +37167550338   Email: aigars@osi.lv
Further Information

Publication History

Received: 12 September 2014

Accepted after revision: 18 October 2014

Publication Date:
14 November 2014 (eFirst)

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

 
  • References and Notes

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