208180-76-1Relevant academic research and scientific papers
Enzymes in organic chemistry VI [1]. Enantioselective hydrolysis of 1-chloroacetoxycycloalkylmethylphosphonates with lipase AP 6 from Aspergillus niger and chemoenzymatic synthesis of chiral, nonracemic 1-aminocyclohexyl-methylphosphonic acids
Wuggenig, Frank,Hammerschmidt, Friedrich
, p. 423 - 436 (1998)
Racemic α-chloroacetoxyphosphonates derived from cycloalkanecarbaldehydes and three branched aldehydes were prepared and tested for kinetic resolution by lipase AP 6 which hydrolyses preferentially the (S) esters. The enantiomeric excess and the reaction rate are significantly influenced by the size of the cycloalkyl group. The optical antipodes of α-hydroxycyclohexylmethylphosphonates (3d; ee 90% and ≥ 99%, respectively) were transformed into the corresponding α-aminophosphonic acids 6.
