Convenient preparation of long-chain dialkyl phosphates: Synthesis of dialkyl phosphates
Reaction of phosphorus oxychloride with a primary alcohol (1.8 equiv) and triethylamine (1.8 equiv) in toluene, followed by filtration and treatment with steam, gives dialkyl phosphates in good yield and essentially free from trialkyl phosphate contamination. Georg Thieme Verlag Stuttgart · New York.
Aitken, R. Alan,Collett, Chris J.,Mesher, Shaun T. E.
experimental part
p. 2515 - 2518
(2012/09/05)
Enantioselective synthesis of trans-aryl-and-heteroaryl-substituted cyclopropylboronates by copper (I)-catalyzed reactions of allylic phosphates with a diboron derivative
A new asymmetric route for the synthesis of trans-2-aryl- and -heteroaryl-substituted cyclopropylboronates has been developed. (Z)-3-arylallylic phosphates were converted to the optically active products with high yield and diastereo- and enantioselectivity through a copper(I)-catalyzed reaction with a diboron derivative. Under mild reaction conditions, the reaction affords the arylcyclopropane products with a functional group and a heteroaromatic group in a highly enantioselective manner. When (E)-allylic phosphates were used as substrates, a ligand-controlled product switch between the trans and cis configurations was observed.