A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates

A Practical and Scalable Synthesis of (S)- and (R)-1-(Dimethoxyphosphoryl)allyl Methyl Carbonates

Abstract The preparation of ( S )- and ( R )-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.

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Veröffentlicht in:Synthesis (Stuttgart) 2015-12, Vol.47 (23), p.3669-3672
Hauptverfasser: Roy, Sudeshna, Sutivisedsak, Nongnuch, Hamper, Bruce C., Lyss, Alexander M., Spilling, Christopher D.
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The preparation of ( S )- and ( R )-1-(dimethoxyphosphoryl)allyl methyl carbonates is achieved on multigram scale from commercially available dimethyl phosphite and acrolein in three steps. The key steps involve an asymmetric Pudovik reaction and enzyme-catalyzed kinetic resolution.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0035-1560487