2,4,6-Triisopropylbenzenesulfonyl azide explained

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.^[1] Introduction of an azide on the α carbon of carboxylic acid derivative 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.

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 .
• Book: 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 .

Notes and References

1. 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 .