Preparation of (cyanomethylene)tributylphosphorane: A new mitsunobu-type reagent
(Cyanomethylene)tributylphosphorane (CMBP), which promoted the alkylation of various nucleophiles (HA) with alcohols (ROH) to give RA (Mitsunobu-type reaction), was prepared in two steps starting from chloroacetonitrile.
A Convenient Method for the Asymmetric Synthesis of Fluorinated α-Amino Acids from Alcohols
Due to their numerous applications, fluorinated amino acids have recently attracted significant attention. The preparation of fluorine-containing phenylalanines, heteroaryl alanines and aliphatic fluorinated amino acids using Mitsunobu-Tsunoda alkylation of a chiral nucleophilic glycine equivalent with readily available alcohol substrates is described. The reaction proceeds in high yields and with excellent diastereoselectivity. This method provides an efficient synthetic route to fluorinated amino acids for which asymmetric approaches are scarce.
Drouet, Fleur,Noisier, Anas F. M.,Harris, Craig S.,Furkert, Daniel P.,Brimble, Margaret A.
supporting information
p. 1195 - 1201
(2015/10/05)
Novel reactivity of stabilized methylenetributylphosphorane: A new mitsunobu reagent
Cyanomethylenetributylphosphorane was shown to mediate the direct condensation of alcohols with O- and N-nucleophiles. A secondary alcohol, 2- octanol, reacted satisfactorily with Walden inversion of its carbinyl carbon.
Tsunoda, Tetsuto,Ozaki, Fumie,Ito, Sho
p. 5081 - 5082
(2007/10/02)
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