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The Detosylation of Chiral 1,2-Bis(tosylamides)

Journal Article


Abstract


  • The deprotection of chiral 1,2-bis(tosylamides) to their corresponding 1,2-diamines is mostly unsuccessful under standard conditions. In a new methodology, the use of Mg/MeOH with sufficient steric additions allows the facile synthesis of 1,2-diamines in 78-98% yields. These results are rationalized using density functional theory and the examination of inner and outer-sphere reduction mechanisms.

Publication Date


  • 2021

Citation


  • Gaston, J. J., Tague, A. J., Smyth, J. E., Butler, N. M., Willis, A. C., van Eikema Hommes, N., . . . Keller, P. A. (2021). The Detosylation of Chiral 1,2-Bis(tosylamides). Journal of Organic Chemistry, 86(13), 9163-9180. doi:10.1021/acs.joc.1c00359

Scopus Eid


  • 2-s2.0-85110097087

Start Page


  • 9163

End Page


  • 9180

Volume


  • 86

Issue


  • 13

Abstract


  • The deprotection of chiral 1,2-bis(tosylamides) to their corresponding 1,2-diamines is mostly unsuccessful under standard conditions. In a new methodology, the use of Mg/MeOH with sufficient steric additions allows the facile synthesis of 1,2-diamines in 78-98% yields. These results are rationalized using density functional theory and the examination of inner and outer-sphere reduction mechanisms.

Publication Date


  • 2021

Citation


  • Gaston, J. J., Tague, A. J., Smyth, J. E., Butler, N. M., Willis, A. C., van Eikema Hommes, N., . . . Keller, P. A. (2021). The Detosylation of Chiral 1,2-Bis(tosylamides). Journal of Organic Chemistry, 86(13), 9163-9180. doi:10.1021/acs.joc.1c00359

Scopus Eid


  • 2-s2.0-85110097087

Start Page


  • 9163

End Page


  • 9180

Volume


  • 86

Issue


  • 13