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. 2009 Jan 3;65(1):17-49.
doi: 10.1016/j.tet.2008.09.083.

An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives

Mario Ordóñez  1 , Haydée Rojas-Cabrera, Carlos Cativiela
Affiliations

An Overview of Stereoselective Synthesis of α-Aminophosphonic Acids and Derivatives

Mario Ordóñez et al. Tetrahedron. .

Abstract

An overview of all methodologies published during the last few years focused to the stereoselective (diastereoselective or enantioselective) synthesis of α-aminophosphonic acids and derivatives is reported. The procedures have been classified according a retrosynthetic strategy and taking into account the formation of each one of the bonds connected to the chiral centre.

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Figures

Figure 1
Figure 1
Conformers for imine (S)-5.
Figure 2
Figure 2
Proposed of addition of LiP(O)(OEt)2to 19.
Figure 3
Figure 3
Intramolecular cyclization of 31.
Figure 4
Figure 4
Addition of LiP(O)(OEt)2 to imine (S)-37.
Figure 5
Figure 5
Transition state for the formation of (SS,SC)-40.
Figure 6
Figure 6
Rationalization for the formation of (SS,RC)-49a-g.
Figure 7
Figure 7
Proposed predominant transition state for phosphonate addition to sulfinimine 37a.
Figure 8
Figure 8
Model proposed for addition of (EtO)3P to 67.
Figure 9
Figure 9
transition state in the formation of 25 and 26.
Figure 10
Figure 10
Transition state prosed for addition of (EtO)2POSiMe3 to (S)-87.
Figure 11
Figure 11
Models for the addition of HP(O)(OEt)2 to 110a.
Figure 12
Figure 12
Models for the addition of HP(O)(OEt)2 to nitrones.
Figure 13
Figure 13
Plausible reaction mechanism of 152a-k.
Figure 14
Figure 14
Proposed mechanism for the addition of (EtO)2P(O)H to 161 catalyzed by quinine.
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