Phosphonylation of 1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine by dialkyl and diaryl phosphonates

Article abstract of DOI:10.1080/10426500802344519

The possibility of using of easily available 1-(α-aminobenzyl)-2- naphthols as chiral auxiliaries in the synthesis of non-racemic α-aminophosphonates has been shown. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/10426500802344519

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Phosphonylation of 1,3-
Diaryl-2,3-dihydro1H-
naphth[1,2-e][1,3]oxazine
by Dialkyl and Diaryl
Phosphonates
Kirill E. Metlushka a , Vladimir A. Alfonsov a ,
Charles E. McKenna b , Boris A. Kashemirov b , Olga
N. Kataeva a , Viktor F. Zheltukhin a , Dilyara N.
Sadkova a & Alexey B. Dobrynin a
a A. E. Arbuzov Institute of Organic and Physical
Chemistry, Kazan Scientific Center of the Russian
Academy of Sciences , Kazan, Russian Federation
b Department of Chemistry , University of Southern
California , Los Angeles, California, USA
Published online: 10 Oct 2008.
To cite this article: Kirill E. Metlushka , Vladimir A. Alfonsov , Charles E. McKenna ,
Boris A. Kashemirov , Olga N. Kataeva , Viktor F. Zheltukhin , Dilyara N. Sadkova &
Alexey B. Dobrynin (2008) Phosphonylation of 1,3-Diaryl-2,3-dihydro1H-naphth[1,2-e]
[1,3]oxazine by Dialkyl and Diaryl Phosphonates, Phosphorus, Sulfur, and Silicon and
the Related Elements, 183:11, 2645-2646
To link to this article: http://dx.doi.org/10.1080/10426500802344519
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Phosphorus, Sulfur, and Silicon, 183:2645–2646, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500802344519
Phosphonylation of 1,3-Diaryl-2,3-dihydro-
1H-naphth[1,2-e][1,3]oxazine by Dialkyl and Diaryl
Phosphonates
Kirill E. Metlushka,1 Vladimir A. Alfonsov,1
Charles E. McKenna,2 Boris A. Kashemirov,2
Olga N. Kataeva,1 Viktor F. Zheltukhin,1
Dilyara N. Sadkova,1 and Alexey B. Dobrynin1
1A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan
Scientific Center of the Russian Academy of Sciences, Kazan, Russian
Federation
2Department of Chemistry, University of Southern California, Los
Angeles, California, USA
The possibility of using of easily available 1-(α-aminobenzyl)-2-naphthols as chiral
auxiliaries in the synthesis of non-racemic α-aminophosphonates has been shown.
Keywords 1-(α-aminobenzyl)-2-naphthol; α-aminophosphonates; chiral
Chiral 1-(α-aminobenzyl)-2-naphthols, known as Betti bases, are avail-
able from the condensation of β-naphthol with benzaldehydes and am-
monia or amines. These compounds are of interest to chemists who work
on asymmetric syntheses and are looking for enantiopure chiral induc-
tors or chiral precursors. Recently, Hu et al.1 reported the resolution
of isolated Betti base as an L-(+)-tartaric acid salt. We report here the
resolution of the Betti base condensation product 1 (formed in situ from
2-naphthol, ammonia and benzaldehyde) using L-(+)-tartaric acid. The
oxazine 1 exists in CDCl3 solution as a mixture of the tautomeric
Received 9 July 2008; accepted 15 July 2008.
This article was presented at the 17th International Conference on Phosphorus Chem-
istry (ICPC-17), April 15–21, Xiamen, China.
This work was supported by the Civilian Research and Development Foundation
(grant no. RUC2-2638-KA-05) and the Russian Foundation for Basic Research (grant
no. 07-03-00617).
Address correspondence to Vladimir Alfonsov, A. E. Arbuzov Institute of Organic and
Physical Chemistry, Russian Academy of Sciences, Arbuzov Str, 8, Kazan, 420088 Russia.
E-mail: alfonsov@iopc.knc.ru
2645

2646
K. E. Metlushka et al.
oxazine and imine forms, resonances of all forms being present in the
1H NMR spectrum.
The products of this reaction are (S)-(+)-1-(α-aminobenzyl)-2-
naphthol tartrate 2, the acetal of benzaldehyde and tartaric acid 3
and (R)-(-)-1,3-diaryl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine, which
can be easily separated by crystallization. The addition reactions of
dialkyl- and diphenylphosphite with racemic and enantiopure 1 and
its 4-arylsubstituted derivatives have also been studied. The reactions
proceed diastereoselectively with formation of aminophosphonates 4.
REFERENCE
[1] Y. Dong, R. Li, J. Lu, X. Xu, X. Wang, and Y. Hu, J. Org. Chem., 70, 8617 (2005).