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Enzymes in Organic Chemistry, Part 2: Lipase-catalysed Hydrolysis of 1-Acyloxy-2-arylethylphosphonates and Synthesis of Phosphonic Acid Analogues of L-Tyrosine
Drescher, Martina,Li, Yong-Fu,Hammerschmidt, Friedrich
, p. 4933 - 4946 (1995)
α-Hydroxyphosphonates (+/-)-3, prepared by base catalysed addition of phosphites 2 to aldehydes 1, were acylated to give esters (+/-)-4.Diethyl 1-acyloxy-2-arylethylphosphonates (+/-)-4a, 4b, and 4e were hydrolysed by lypase from Aspergillus niger in a biphasic system to afford (R)-α-hydroxyphosphonates of low enantiomeric purity.The corresponding diisopropyl phosphonates (+/-)-4c, 4f and 4g gave (S)-α-hydroxyphosphonates with an ee of up to 78percent.The absolute configuration of the α-hydroxyphosphonates was assigned by 31P NMR spectroscopy of their (R)-MTPA-esters. (S)-3b and 3e were chemically transformed via their azides to phosphonic acid analogues of L-phenylalanine and L-tyrosine, respectively.
