A highly efficient asymmetric synthesis of β-aminophosphonic acids, via addition of α-phosphonate carbanions to chiral, enantiopure sulfinimines

M Mikołajczyk, P Łyżwa, J Drabowicz…

Index: Mikolajczyk, Marian; Lyzwa, Piotr; Drabowicz, Jozef; Wieczorek, Michal W.; Blaszczyk, Jaroslaw Chemical Communications, 1996 , # 13 p. 1503 - 1504

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Citation Number: 20

Abstract

Addition of α-phosphonate carbanions to (S)-sulfinimines 1 affords N-sulfinyl β- aminophosphonates 2 in a diastereoisomeric ratio from 5: 1 to 10: 1; the major diastereoisomers of 2, after separation, are converted to the corresponding β- aminophosphonates 3 or to (+)-β-amino-β-phenylethane phosphonic acid 4, whose absolute configuration was established as (R) by X-ray crystallography.