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Issue 94, 2012
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Efficient asymmetric synthesis of trifluoromethylated β-aminophosphonates and their incorporation into dipeptides

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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


Submitted
14 Sep 2012
Accepted
09 Oct 2012
First published
09 Oct 2012

Chem. Commun., 2012,48, 11519-11521
Article type
Communication

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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