2,4,6-Triisopropylbenzenesulfonyl azide

Trisyl azide.png 2,4,6-Tri(propan-2-yl)benzene-1-sulfonyl azide 36982-84-0 correct CAS 1995382 2391566 DTXSID80327323 609-323-7 1S/C15H23N3O2S/c1-9(2)12-7-13(10(3)4)15(14(8-12)11(5)6)21(19,20)18-17-16/h7-11H,1-6H3 AEMWUHCKKDPRSK-UHFFFAOYSA-N 371707 CC(C)C1=CC(=C(C(=C1)C(C)C)S(=O)(=O)N=[N+]=[N-])C(C)C 15 23 3 2 1 39–44 2,4,6-Triisopropylbenzenesulfonyl azide https://pubchem.ncbi.nlm.nih.gov/compound/371707#section=Safety-and-Hazards pubchem.ncbi.nlm.nih.gov 1 May 2022 en 01 06 Danger 241 301 210 234 240 261 264 264+265 270 271 280 301+316 302+352 304+340 305+351+338 319 321 330 332+317 337+317 362+364 370+380+375[+378] 403 403+233 405 410 411 420 501 2,4,6-Triisopropylbenzenesulfonyl azide (trisyl azide) is an organic chemical used as a reagent to supply azide for electrophilic amination reactions, such as for the asymmetric synthesis of unnatural amino acids.Evans David A. Britton Thomas C. 1987 Electrophilic azide transfer to chiral enolates. A general approach to the asymmetric synthesis of α-amino acids J. Am. Chem. Soc. 109 22 6881–3 10.1021/ja00256a069 1987JAChS.109.6881E Introduction of an azide on the α carbon of carboxylic acid derivatives using trisyl azide is an efficient alternative to electrophilic halogenation followed by nucleophilic substitution using anionic azide. Using an oxazolidinone as chiral auxiliary typically gives good induction of the stereochemistry at the α position. Subsequent reduction converts the α-azide to an α-amine. File:Evans asymmetric azide.png References Further reading Calmes M. Daunis J. How to build optically active α-amino acids Amino Acids 16 215–250 1999 3–4 10.1007/BF01388170 10399014 36591079 Han Y. Lin J. Liao S. Qiu W. Cai C. Hruby V.J. 2002 Stereoselective synthesis of highly topographically constrained β-isopropyl substituted aromatic amino acids Tam J.P. Kaumaya P.T.P. Peptides Frontiers of Peptide Science American Peptide Symposia 5 241–243 Springer 10.1007/0-306-46862-X_98 0-7923-5160-6 Category:Arylsulfonamides Category:Organoazides Category:Reagents for organic chemistry Category:Isopropyl compounds