Asymmetric Synthesis of β‑Hydroxyphosphonates via a Chemoenzymatic Cascade

Chiral β-hydroxyphosphonates are essential building blocks for organophosphorus compounds. However, the asymmetric synthesis of these units remains a significant challenge. Herein, we describe a one-pot chemoenzymatic cascade process to access chiral β-hydroxyphosphonates, which combines photo-oxida...

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Bibliographic Details
Published in:Organic letters 2024-07, Vol.26 (26), p.5458-5462
Main Authors: Fang, Jiali, Ren, Hanwen, Xu, Shaowu, Huang, Chenming, Jiang, Yingqian, Zhang, Wenhe, You, Song, Qin, Bin
Format: Article
Language:English
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Summary:Chiral β-hydroxyphosphonates are essential building blocks for organophosphorus compounds. However, the asymmetric synthesis of these units remains a significant challenge. Herein, we describe a one-pot chemoenzymatic cascade process to access chiral β-hydroxyphosphonates, which combines photo-oxidative chemical reactions and bioreductions. The incorporation of photooxidation in the chemical reaction resulted in up to 92% yield and >99% enantiomeric excess (ee) of β-hydroxyphosphonates in the cascade. In addition, the scale-up of diethyl (S)-(2-hydroxy-2-phenylethyl)­phosphonate demonstrates the potential application of this strategy.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c01716