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Direct Functionalization of Lithium Phosphine Oxides Bearing an Alkyne Chain

Von Wiley-VCH zur Verfügung gestellt

Selective hydrophosphorylation of carbonyl bonds was developed via a lithium phosphine oxide intermediate, resulting in intermolecular addition to an aldehyde, instead of the intramolecular cyclisation pathway. Valuable alkynyl phosphorated alcohols were obtained in good yields and moderate diastereoselectivity.


Abstract

An efficient synthesis of functionalized alkynyl phosphine oxides is described. The current approach is based on the activation of the phosphorus−hydrogen bond (P−H bond) of a secondary phosphine oxide. After the deprotonation step using n-butyllithium, the in-situ generated LiP(O)RR’ undergoes further condensation with a wide variety of electrophiles, and without a cyclisation step into the alkyne as a side reaction. In particular, the addition to aldehydes proceeds quickly and gives access to α-hydroxy phosphine oxides, with a diastereoselectivity rate up to 80/20.

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