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An efficient route to chiral alpha- and beta-hydroxyalkanephosphonates.
1Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, SE-10691 Stockholm, Sweden. pamies@organ.su.se
The Journal of Organic Chemistry
|June 7, 2003
Summary
This study presents a dynamic kinetic resolution method for hydroxyphosphonates using enzymatic resolution and ruthenium catalysis. The process efficiently converts racemic compounds into enantiomerically pure acetates with high yields and purity.
Area of Science:
- Organic Chemistry
- Catalysis
- Biocatalysis
Background:
- Hydroxyphosphonates are important building blocks in organic synthesis.
- Enantiomerically pure compounds are crucial for pharmaceuticals and agrochemicals.
- Developing efficient methods for chiral resolution is a key challenge.
Purpose of the Study:
- To develop a novel dynamic kinetic resolution (DKR) strategy for alpha- and beta-hydroxyphosphonates.
- To combine enzymatic kinetic resolution with ruthenium-catalyzed alcohol isomerization.
- To achieve high enantioselectivity and yield in the transformation of racemic hydroxyphosphonates.
Main Methods:
- Enzymatic kinetic resolution of racemic hydroxyphosphonates.
- Ruthenium-catalyzed isomerization of alcohols.
- Integration of enzymatic and catalytic steps for dynamic kinetic resolution.
- Acetylation of resolved hydroxyphosphonates.
Main Results:
- Successful implementation of a combined enzymatic and catalytic DKR process.
- Efficient transformation of various racemic hydroxyphosphonates.
- Attainment of high enantiomeric excess (ee) up to 99% for the resulting acetates.
- Achieved yields up to 87% in the DKR process.
Conclusions:
- The developed DKR strategy is highly effective for producing enantiomerically pure hydroxyphosphonate acetates.
- This method offers a valuable tool for accessing chiral phosphonate derivatives.
- The combination of biocatalysis and chemocatalysis provides a powerful approach for asymmetric synthesis.