- Conversion of nitriles to 1-aminophosphonic acids and preparation of phosphahomocysteines of high enantiomeric excess
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A variety of nitriles was reduced to diisobutylaluminum salts of aldimines, to which diisopropyl phosphite was added. The corresponding 1-aminophosphonates were either deprotected to give racemic 1-aminophosphonic acids or reacted with Boc2O to yield N-Boc-protected 1-aminophosphonates. The enantiomers of 2-benzylthio-1-(t-butoxycarbonylamino)propylphosphonate were obtained from the racemate by chiral HPLC and converted to phosphonic acid analogs of (R)- and (S)-homocysteine, (R)- and (S)-2-aminobutyric acid and (S)-methionine, all of ee >97% as determined by chiral HPLC.
- Qian, Renzhe,Horak, Jeannie,Hammerschmidt, Friedrich
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p. 737 - 744
(2017/06/05)
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- Asymmetric synthesis of α-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines
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A simple and general asymmetric synthesis of α-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-α-substituted amino phosphonic acids in good overall yields and high ee (77→97%) after simple deprotection.
- Maury, Catherine,Gharbaoui, Tawfik,Royer, Jacques,Husson, Henri-Philippe
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p. 3687 - 3693
(2007/10/03)
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- Electrophilic amination and azidation of chiral α-alkyl phosphonamides: Asymmetric syntheses of α-amino α-alkyl phosphonic acids
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Stereoselective electrophilic aminations of chiral non racemic α-alkyl phosphonamides, derived from N,N'-dimethyl (R,R)-1,2-diaminocyclohexane, proceed with moderate to excellent enantioselectivities. The products are hydrolyzed and reduced to the corresponding α-alkyl α-amino phosphonic acids. The sense of asymmetric induction was confirmed by X-ray crystal structure analysis.
- Hanessian,Bennani
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p. 1272 - 1274
(2007/10/02)
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- A simple and general method for the asymmetric synthesis of α-aminophosphonic acids
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A simple and general method for the asymmetric synthesis of α-aminophosphonic acids is described. A chiral phosphonate prepared in one step from R-(-)-phenylglycinol was alkylated with good diastereoselectivity using different electrophiles.
- Maury,Royer,Husson
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p. 6127 - 6130
(2007/10/02)
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- A versatile asymmetric synthesis of α-amino α-alkyl-phosphonic acids of high enantiomeric purity
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A general protocol for the synthesis of α-amino-α- alkyl phosphonic acids in either enantiomeric form is described based on the alkylation of chiral bicyclic phosphonamides derived from (R,R)- and (S,S)-1,2-diaminocyclohexane.
- Hanessian, Stephen,Bennani, Youssef L.
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p. 6465 - 6468
(2007/10/02)
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