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Synthesis of both RP and SP enantiomers of unsymmetrical methylphosphonates based on a new approach utilizing a P-ester bond with α-hydroxyacids by Piotr Bałczewski; Aldona Szadowiak; Tomasz Białas; Wanda M. Wieczorek; Agnieszka Balińska is a Chemistry article available to read on EtoBox.

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Condensation of methyl methylphosphonochloridate with the dilithium salt of 2-methyllactic acid gave P-racemic methylphosphonates which unexpectedly contained two units of a-hydroxyacid linked via carboxylic ester bond. The racemic mixture was chromatographically separated via diastereomeric salts with quinine or cinchonine to give, based on the X-ray analysis, pure (R P )-( +) and (S P )-(À) enantiomers. Both enantiomers were immobilized on the ArgoGel Ò -OH solid support. Condensation of methyl methylphosphonochloridate with a-hydroxyacid methyl esters [2-methyllactate, (S C )-(À)-lactate, methyl (S C )-(+) and (R C )-(À)-mandelates] gave chromatographically inseparable 1:1 mixtures of diastereomers in 63-69% yields. A basic hydrolysis of the latter resulted in a selective and unexpected cleavage of the P-OMe group in a quantitative yield [(S C )-(+) and (R C )-(À)-mandelates, (S C )-(À)-lactate] or simultaneous cleavages of P-OMe and C(O)OMe groups (2-methyllactate).

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Author

Piotr Bałczewski; Aldona Szadowiak; Tomasz Białas; Wanda M. Wieczorek; Agnieszka Balińska

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0957-4166)

Published

2006

Language

EN

Field

Chemistry (Physical Sciences)