Methylprenyl and Prenyl Protection for Sulfonamides

Anna Nikitjuka; Aleksandra Nekrasova; Aigars Jirgensons

doi:10.1055/s-0034-1379428

Synlett, Table of Contents

Synlett 2015; 26(02): 183-186
DOI: 10.1055/s-0034-1379428

letter

Methylprenyl and Prenyl Protection for Sulfonamides

Anna Nikitjuka

Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga 1006, Latvia Fax: +37167550338 Email: aigars@osi.lv

,

Aleksandra Nekrasova

Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga 1006, Latvia Fax: +37167550338 Email: aigars@osi.lv

,

Aigars Jirgensons*

Latvian Institute of Organic Synthesis, Aizkraukles 21, Riga 1006, Latvia Fax: +37167550338 Email: aigars@osi.lv

› Author Affiliations

Abstract

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Dedicated to Dr. Valerjans Kauss on the occasion of his 60^th 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.

Key words

sulfonamides - protecting groups - allylation - cations - cleavage

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References

References and Notes
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