Mario Ordóñez

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Victoria Labastida-Galván

Mahesh Kasthuri

Egle Beccalli

Università degli Studi di Milano - State University of Milan (Italy)

Oliver Reiser

Universität Regensburg

Christopher J. Richards

University of East Anglia

Ramon Bosque

Christopher Spilling

University of Missouri - St. Louis

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Universidad de Valladolid

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Joan Albert

Universitat de Barcelona

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Papers by Mario Ordóñez

Preparation of ( R)- and ( S)-γ-amino-β-hydroxypropylphosphonic acid from glycine

Tetrahedron-asymmetry, 2003

An efficient synthesis of both enantiomers of g-amino-b-hydroxypropylphosphonic acid, an analogue... more

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Highly diastereoselective reduction of β-ketophosphonates bearing homochiral bis(α-methylbenzyl)amine: preparation of both enantiomers of phosphogabob (GABOB P

Tetrahedron-asymmetry, 2004

The reduction of dimethyl 3-N,N-di(a-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane ... more The reduction of dimethyl 3-N,N-di(a-methylbenzyl)amino-2-ketophosphonates 9 with catecholborane at À78°C in presence of LiClO 4 , gave c-amino-b-hydroxyphosphonates 10 and 11 in good yield and with excellent diastereoselectivity. This procedure represents an example of highly diastereoselective 1,4-induction. The hydrolysis and hydrogenation of 10 and 11 afforded the (R)-and (S)-c-amino-b-hydroxypropylphosphonic acid (GABOB P ), respectively.

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Stereoselective synthesis of GABOB, carnitine and statine phosphonates analogues

Tetrahedron-asymmetry, 2010

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A practical synthesis of syn- and anti-α,β-dihydroxyphosphinates via diastereoselective reduction of α-phosphinoyl ketones

Tetrahedron-asymmetry, 2008

Reduction of b-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH 4 in m... more Reduction of b-keto-diphenylphosphine oxide (S)-4 derived from (S)-mandelic acid with NaBH 4 in methanol at À78°C gave the anti-3-diphenylphosphinoyl-1,2-diol 6, whereas the reduction of (S)-4 with Zn(BH 4 ) 2 in THF at À78°C afforded the syn-1,2-diol 5, both in high yield and excellent diastereoselectivity. This procedure represents a new approach to the diastereoselective synthesis of diphenylphosphinoyl diols and an example of highly diastereoselective 1,2-induction. A theoretical model to explain the direction and degree of asymmetric induction is proposed.

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Efficient and Practical Synthesis of syn- and anti-b,g- Dihydroxyphosphonates Derived from (S)-Mandelic Acid

A new efficient and practical synthesis of syn-and antib,g-dihydroxyphosphonates 1 and 2 was deve... more A new efficient and practical synthesis of syn-and antib,g-dihydroxyphosphonates 1 and 2 was developed in high diastereoselectivity via reduction of b-ketophosphonates readily obtained from (S)-mandelic acid. An example of "diastereoselective 1,2-induction" is showed and a mechanistic model to explain the stereochemical outcome is proposed. Assignment of the configuration at the new stereogenic centers was achieved by 1 H NMR spectral data of their corresponding acetonides.

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Diastereoselective reduction of β-ketophosphonates derived from amino acids. A new entry to enantiopure β-hydroxy-γ-aminophosphonate derivatives

Tetrahedron-asymmetry, 2002

The reduction of g-N,N-dibenzylamino-b-ketophosphonates 4 derived from readily available (S)-trib... more The reduction of g-N,N-dibenzylamino-b-ketophosphonates 4 derived from readily available (S)-tribenzylated amino acids was achieved with catecholborane at -20°C affording g-amino-b-hydroxyphosphonates 5 in high diastereoselectivity and good chemical yield. These reactions provide a new entry to enantiomerically pure g-amino-b-hydroxyphosphonates.

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Recent progress on the stereoselective synthesis of cyclic quaternary α-amino acids

Tetrahedron-asymmetry, 2009

The most recent papers describing the stereoselective synthesis of cyclic quaternary α-amino acid... more

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Highly diastereoselective addition of Et 2AlCN to β-keto amides derived from ( S)-4-isopropyl-2-oxazolidinone

Tetrahedron-asymmetry, 2003

The addition of Et 2 AlCN in the presence of ZnBr 2 or Et 2 AlCl to 1,3-dicarbonyl compounds deri... more The addition of Et 2 AlCN in the presence of ZnBr 2 or Et 2 AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral b-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins.

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Preparation of Phosphostatine Analogues From L-amino acids

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Preparation of dimethyl ( R)- and ( S)-2-(2-aminophenyl)-2-hydroxyethylphosphonate from anthranilic acid

Tetrahedron-asymmetry, 2004

An efficient synthesis of both enantiomers of dimethyl d-amino-b-hydroxyethylphosphonate 6 has be... more An efficient synthesis of both enantiomers of dimethyl d-amino-b-hydroxyethylphosphonate 6 has been achieved starting from anthranilic acid, through the resolution of dimethyl (±)-2-(2-N,N-dibenzylaminophenyl)-2-hydroxyethylphosphonate 9 with (S)-O-methylmandelic acid. The absolute configuration of the enantiomers 9 was assigned by the Dale and Mosher approach using the extended Newman projections and molecular mechanics.

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One-pot three-component highly diastereoselective synthesis of isoindolin-1-one-3-phosphonates under solvent and catalyst free-conditions

Tetrahedron-asymmetry, 2011

The one-pot three-component reaction of 2-formylbenzoic acid with (S)-and (R)-methylbenzylamine a... more The one-pot three-component reaction of 2-formylbenzoic acid with (S)-and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1 0 S)-and (3S,1 0 R)-isoindolin-1-one-3-phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO 2 H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity.

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Stereoselective synthesis of γ-amino acids

Tetrahedron-asymmetry, 2007

c-Amino acids have attracted considerable attention as biologically active compounds in the centr... more c-Amino acids have attracted considerable attention as biologically active compounds in the central nervous system (CNS) of mammals. Over the last few years, significant interest in the stereoselective synthesis and practical application of linear and cyclic chiral camino acids in the synthesis and design of a,b-and b,c-hybrid peptides with definite secondary structures and design of nanotubes has been reported, thus demonstrating the theoretical interest and the practical importance of c-amino acids. An overview of synthetic approaches to linear and cyclic chiral c-amino acids and derivatives is presented. Data on the practical applications of c-amino acids are also discussed.

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An overview of stereoselective synthesis of α-aminophosphonic acids and derivatives

Tetrahedron, 2009

An overview of all methodologies published during the last few years focused to the stereoselecti... more 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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A convenient method for the preparation of chiral phosphonoacetamides and their Horner–Wadsworth–Emmons reaction

Tetrahedron-asymmetry, 2007

Chiral phosphonoacetamides bearing (S)-(α-methylbenzyl)benzylamine, (S,S)-bis(α-methylbenzyl )ami... more