Issue 94, 2012
From the journal:

Chemical Communications

Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides†

Kostiantyn V. Turcheniuk,a   Kateryna O. Poliashko,a   Valery P. Kukhar,a   Alexander B. Rozhenko,b   Vadim A. Soloshonokcd  and  Alexander E. Sorochinsky*acd  

* Corresponding authors

a Institute of Bioorganic Chemistry & Petrochemistry, National Academy of Sciences of Ukraine, 1 Murmanskaya, Kiev, Ukraine
E-mail: sorochinsky@bpci.kiev.ua
Fax: +380 44 573-25-31
Tel: +380 44 558-25-52

b Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanskaya, Kiev, Ukraine

c Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018 San Sebastian, Spain

d Basque Foundation for Science, Bilbao, Spain

Abstract

Addition of anions derived from dialkyl methylphosphonates to (Ss)-N-tert-butanesulfinyl (3,3,3)-trifluoroacetaldimine afforded (Ss,R) addition adducts in moderate to good yield (53–75%) with excellent diastereoselectivity (94–95% de). After selective removal of the N-sulfinyl group, dipeptides containing enantiomerically pure diethyl 2-amino-3,3,3-trifluoropropylphosphonate were synthesized to investigate the influence of the trifluoromethyl substituent on N-terminal coupling.

Graphical abstract: Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides

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Article information

DOI
https://doi.org/10.1039/C2CC36702E
Article type
Communication
Submitted
14 Sep 2012
Accepted
09 Oct 2012
First published
09 Oct 2012

Chem. Commun., 2012,48, 11519-11521

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Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides

K. V. Turcheniuk, K. O. Poliashko, V. P. Kukhar, A. B. Rozhenko, V. A. Soloshonok and A. E. Sorochinsky, Chem. Commun., 2012, 48, 11519 DOI: 10.1039/C2CC36702E

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