Alkylation of Phosphinite/Phosphonite-Boranes via Temporary Protection of the P–H Bond

Kamil Modzelewski; Sylwia Sowa

doi:10.1055/s-0040-1707104

Synthesis, Table of Contents

Synthesis 2020; 52(16): 2410-2426
DOI: 10.1055/s-0040-1707104

paper

Alkylation of Phosphinite/Phosphonite-Boranes via Temporary Protection of the P–H Bond

Kamil Modzelewski

,

Sylwia Sowa ∗

Department of Organic Chemistry, Faculty of Chemistry, Institute of Chemical Sciences, Marie Curie-Sklodowska University in Lublin, 33 Gliniana St., Lublin 20-614, Poland Email: sylwia.sowa@poczta.umcs.lublin.pl

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Abstract

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Abstract

A new alkylation protocol for the synthesis of tertiary phosphonite/phosphinite-boranes is developed. P-Alkylation products are obtained exclusively in moderate to very good yields from easily accessible (1-hydroxy-1-methylethyl)/(1-hydroxy-1-cyclohexyl) phosphonite/phosphinite-boranes upon reaction with a variety of electrophiles under mild conditions. The methodology opens up new synthetic routes for organophosphorus chemistry and offers access to valuable alkyl phosphonite/phosphinite-boranes. In contrast to previously reported oxidative removal–substitution sequences for the preparation of optically active phosphinite-boranes, our protocol provides a one-step procedure that occurs without loss of stereochemical information at phosphorus. This new approach provides a rather advantageous protocol when compared to direct alkylation methods (which may undergo P-epimerization) and occurs in a stereoselective manner even at 0 °C.

Key words

alkylation - chemoselectivity - protecting group - in situ deprotection - phosphinite-boranes - phosphonite-boranes - diastereoselectivity

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References

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