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

Sudeshna Roy; Nongnuch Sutivisedsak; Bruce C. Hamper; Alexander M. Lyss; Christopher D. Spilling

doi:10.1055/s-0035-1560487

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

Sudeshna Roy, Nongnuch Sutivisedsak, Bruce C. Hamper, Alexander M. Lyss, Christopher D. Spilling

University of Missouri-St. Louis

Research output: Contribution to journal › Article › peer-review

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.

Original language	American English
Journal	Synthesis
Volume	47
DOIs	https://doi.org/10.1055/s-0035-1560487
State	Published - Oct 21 2015

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Organic Chemistry

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title = "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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AU - Sutivisedsak, Nongnuch

AU - Hamper, Bruce C.

AU - Lyss, Alexander M.

AU - Spilling, Christopher D.

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AB - 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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M3 - Article

VL - 47

JO - Synthesis

JF - Synthesis

ER -

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

Abstract

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