Two-Step Transesterification of Phosphates, Phosphorothioates, and Phosphonates with a Binaphthyl Group for the Synthesis of P-Chirogenic Phosphates and Phosphonates

Chikako Endo; Yurika Inoue; Toshifumi Maruyama; Mao Minoura; Toshiaki Murai

doi:10.1055/a-1948-3003

Synthesis, Table of Contents

Synthesis 2023; 55(06): 934-944
DOI: 10.1055/a-1948-3003

special topic

Synthetic Advancements Enabled by Phosphorus Redox Chemistry

Two-Step Transesterification of Phosphates, Phosphorothioates, and Phosphonates with a Binaphthyl Group for the Synthesis of P-Chirogenic Phosphates and Phosphonates

Chikako Endo

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Yurika Inoue

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Toshifumi Maruyama

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

,

Mao Minoura

^bDepartment of Chemistry, College of Science, Rikkyo University, Nishi-ikebukuro, Toshima-ku, Tokyo, 171-8501, Japan

,

Toshiaki Murai∗

^aDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan

› Author Affiliations

Abstract

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Abstract

Two-step transesterification of four-coordinate pentavalent organophosphorus compounds with a binaphthyl group has been studied in detail. The first step involves transfer of the axial chirality of a hydroxybinaphthyl group to the central chirality of the phosphorus atom. The second step is the substitution reaction of P-chirogenic compounds with a hydroxybinaphthyl group with lithium alkoxides, leading to the formation of P-chirogenic phosphates and phosphonates with primary and secondary alkoxy groups.

Key words

P–O bond formation - transesterification - P-chirogenic phosphates - P-chirogenic phosphonates - axis-to-center chirality transfer

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References

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Recent examples of P-chirogenic oligonucleotides, see:

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