The construction of three C–P bonds of P-stereogenic tertiary phosphines containing (l)-menthyl

Abstract

<p>A wide range of <italic>R</italic>_P or <italic>S</italic>_P-(<sc>l</sc>)-menthyl-containing SPOs were prepared <italic>via</italic> the reaction of 1,1′-bi(2-naphthol) derived phosphonite with a metallic reagent with excellent yield and dr.</p>

Electrochemical Phosphorylation of Organic Molecules

“…Generally, the most common paths for the construction of PÀ C and PÀ X (X=N, O, S and Se) bonds proceed by the nucleophilic substitution of toxic halides with ROH/RSX, [9] Friedel-Crafts reaction, [10] Michaelis-Arbuzov reaction [11] and also with the use of organometallic and a phosphine. [12] Likewise, phosphorus reagents can be applied as nucleophilic species for the formation of new bonds, starting for example from dialkyl-or diaryl-phosphine oxides, phosphonates esters, hypophosphite, phosphines, phosphine-borane, among others. [13][14][15][16] In general, these strategies can follow a direct phosphorylation in heterocycles, involving the crosscoupling between halides or alcohols of aryl or alkyl, and can also proceed to phospha-aldol, phospha-Michael or phospha-Mannich reactions.…”

“…Considering this, the development of new strategies for obtaining new P−C and P−heteroatom bonds is of great interest, expanding the application possibilities. Generally, the most common paths for the construction of P−C and P−X (X=N, O, S and Se) bonds proceed by the nucleophilic substitution of toxic halides with ROH/RSX, [9] Friedel‐Crafts reaction, [10] Michaelis‐Arbuzov reaction [11] and also with the use of organometallic and a phosphine [12] . Likewise, phosphorus reagents can be applied as nucleophilic species for the formation of new bonds, starting for example from dialkyl‐ or diaryl‐phosphine oxides, phosphonates esters, hypophosphite, phosphines, phosphine‐borane, among others [13–16] .…”

Cleavage of Aromatic C–O Bonds via Intramolecular SNAr Reaction and Preparation of P,C,Axial-Stereogenic Menthyl Phosphine Derivatives

“…We were engaged in developing facile routes to acquire MSPBs . The enclosed work presented a procedure that utilized ( L )-menthyl to induce the chiralities on phosphorus, carbon, and axis.…”