Asymmetric synthesis of phosphonotrifluoroalanine and its derivatives using N-tert-butanesulfinyl imine derived from fluoral

作者：Roeschenthaler Gerd Volker; Kukhar Valery P; Kulik Irine B; Belik Michael Yu; Sorochinsky Alexander E^*; Rusanov Eduard B; Soloshonok Vadim A

来源：Tetrahedron Letters, 2012, 53(5): 539-542.

DOI：10.1016/j.tetlet.2011.11.096

• Fluorine
• Phosphites
• Imines
• Aminophosphonic acids
• Addition
• Asymmetric synthesis

Addition of dialkyl phosphites to (S)-N-tert-butanesulfinyl imine derived from fluoral afforded, under mild conditions, the corresponding N-tert-butanesulfinyl alpha-aminophosphonates in moderate to high yields and diastereoselectivity. The major diastereomers of N-tert-butanesulfinyl alpha-arninophosphonates of (S-s,S) configuration were isolated, and after partial or complete deprotection, converted into enantiomerically pure phosphonotrifluoroalanine and its dialkyl esters.

• 出版日期2012-2-1