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

Gaston JJ, Tague AJ, Smyth JE, Butler NM, Willis AC, van Eikema Hommes N, Yu H, Clark T, Keller PA (2021)

Publication Language: English

Publication Type: Journal article

Publication year: 2021

Journal

Journal of Organic Chemistry American Chemical Society

Book Volume: 86

Pages Range: 9163-9180

Journal Issue: 13

DOI: 10.1021/acs.joc.1c00359

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.

Authors with CRIS profile

Nicolaas van Eikema Hommes Computer-Chemie-Centrum Timothy Clark Computer-Chemie-Centrum

Involved external institutions

University of Wollongong (UOW) AU Australia (AU) Australian National University (ANU) AU Australia (AU)

How to cite

APA:

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. https://dx.doi.org/10.1021/acs.joc.1c00359

MLA:

Gaston, Jayden J., et al. "The Detosylation of Chiral 1,2-Bis(tosylamides)." Journal of Organic Chemistry 86.13 (2021): 9163-9180.

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