# Stereoselective additions to alkenylphosphonium salts for the synthesis of P-stereogenic compounds

## TL;DR

This paper introduces a new method to create chiral organophosphorus compounds using BINOL-based alkenylphosphonium salts for efficient and selective synthesis.

## Contribution

A novel BINOL-based approach for stereoselective synthesis of P- and C-stereogenic compounds in a single step.

## Key findings

- BINOL-based alkenylphosphonium salts enable the formation of two non-consecutive stereogenic centers.
- The method achieves high yield and stereoselectivity in the synthesis of organophosphorus compounds.
- These salts act as activated alkenylphosphonamidate surrogates with improved reactivity and stereocontrol.

## Abstract

The stereoselective functionalisation of alkenyl P(v) compounds via conjugate additions represents an attractive approach to synthesise chiral organophosphorus compounds. However, asymmetric conjugate additions to alkenyl P(v) compounds are scarce and, in the presence of P-stereogenic centers, diastereoinduction is often low. Here, we report the use of BINOL-based alkenylphosphonium salts for the generation of two non-consecutive P- and C-stereogenic centers via addition of C-nucleophiles in a single operation. These alkenylphosphonium salts behave as activated alkenylphosphonamidate surrogates with increased reactivity and stereocontrol. This methodogy allows the versatile preparation of enantioenriched organophosphorus building-blocks in high yield and stereoselectivity.

BINOL-based alkenylphosphonium salts enable highly stereoselective C-nucleophile additions, delivering P- and C-stereogenic organophosphorus compounds in a single operation with high yield and stereocontrol.