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

Publication Name

Journal of Organic Chemistry

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.

Open Access Status

This publication is not available as open access

Volume

86

Issue

13

First Page

9163

Last Page

9180

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Link to publisher version (DOI)

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