Erratum: N-amination of amino acids and its derivatives using N-Boc-O-tosyl hydroxylamine as an efficient NH-Boc transfer reagent: Electrophilic amination (Tetrahedron Letters (2012) 53 (2292-2294))

Full text of DOI:10.1016/j.tetlet.2013.11.075

Tetrahedron Letters 55 (2014) 561–563
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Corrigendum
Corrigendum to ‘N-amination of amino acids and its derivatives
using N-Boc-O-tosyl hydroxylamine as an efficient NH-Boc transfer
reagent: electrophilic amination’ [Tetrahedron Lett. 53 (2012)
2292–2294]
Thankappan Baburaj a, Sivalingam Thambidurai b,
⇑
a Anthem Biosciences Pvt. Ltd, No. 49, Canara Bank Road, Bommasandra Industrial Area, Phase I, Bangalore 560 099, India
b Department of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
In our published Letter we have reported the formation of
hydrazino acid derivatives by electrophilic amination using
N-Boc-O-tosyl hydroxylamine. From the available literature (Vidal
et al., Chem. Eur. J. 1997, 3, 169, Krause et al., Tetrahedron Lett. 2010,
51, 3568, Hartmann, W. Synthesis 1988, 807 and Armstrong et al.,
Org. Lett. 2005, 7, 713) and Prof. Alan Armstrong’s comments, we
conclude that the structures assigned were erroneous and the
correct products are the isomeric urea derivatives formed by a
reaction via Lossen rearrangement as in Scheme 1.
The correct structures of products are given in Tables 1 and 2.
We thank Prof. Alan Armstrong for his valuable comments.
Scheme 1.
Table 1
Electrophilic N-amination of a-amino acids by 5
Entry
1
Aminoacid (6a–j)
Product (7a–j)
Corrected structure
2
3
(continued on next page)
q DOI of original article: http://dx.doi.org/10.1016/j.tetlet.2012.02.075
⇑
Corresponding author. Tel.: +91 94420 47766; fax: +91 4565 225 202.
E-mail address: sthambi01@yahoo.co.in (S. Thambidurai).
0040-4039/$ - see front matter Ó 2013 Elsevier Ltd. All rights reserved.
http://dx.doi.org/10.1016/j.tetlet.2013.11.075

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T. Baburaj, S. Thambidurai / Tetrahedron Letters 55 (2014) 561–563
Table 1 (continued)
Entry
Aminoacid (6a–j)
Product (7a–j)
Corrected structure
4
5
6
7
8
9
10
Table 2
Electrophilic N-amination of amino acid derivatives by 5
Entry
1
Substrate (8a–l)
Product (9a–l)
Corrected structure
2
3
4
5
6
7

T. Baburaj, S. Thambidurai / Tetrahedron Letters 55 (2014) 561–563
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Table 2 (continued)
Entry
Substrate (8a–l)
Product (9a–l)
Corrected structure
8
9
10
11
12