کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
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1327460 | 977484 | 2005 | 9 صفحه PDF | دانلود رایگان |

Aminophosphonic acids have become increasingly important in different fields of chemistry, medicine and agriculture. This account outlines the results obtained in the author’s laboratory on the asymmetric synthesis of acyclic and cyclic aminophosphonic acids mediated by chiral sulfinyl auxiliary. A key reaction in the synthesis of enantiopure α- and β-aminoalkanephosphonic acids involving a highly diastereoselective addition of phosphite anions or α-phosphonate carbanions to enantiopure sulfinimines is discussed. The asymmetric cyclopropanation of enantiopure α-phosphorylvinyl sulfoxides with sulfur ylides is presented as a platform for developing a new approach to optically active β-aminocyclopropanephosphonic acids. It is exemplified by the total synthesis of enantiopure β-amino-γ-phenylcyclopropanephosphonic acid – a constrained analogue of the GABAB antagonist phaclofen.
A new, general approach to enantiomericaly pure α- and β-aminoalkanephosphonic acids is described which involves in a key step a highly diastereoselective addition of phosphite anions and α-phosphonate carbanions to enantiopure sulfinimines. This account discusses also the asymmetric cyclopropanation of enantiopure α-phosphorylvinyl sulfoxides which paved the way to β-aminocyclopropanephosphonic acids. This new approach is exemplified by the total synthesis of β-amino-γ-phenylcyclopropanephosphonic acid – a constrained analogue of the GABAB antagonist phaclofen.Figure optionsDownload as PowerPoint slide
Journal: Journal of Organometallic Chemistry - Volume 690, Issue 10, 16 May 2005, Pages 2488–2496