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

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

Publication History

Received: 22 July 2022

Accepted: 21 September 2022

Accepted Manuscript online:
21 September 2022

Article published online:
03 November 2022

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Recent examples of P-chirogenic oligonucleotides, see:
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