874280-90-7Relevant academic research and scientific papers
Phosphinamide-directed benzylic lithiation. application to the synthesis of peptide building blocks
Burgos, Pascual Ona,Fernandez, Ignacio,Iglesias, Maria Jose,Garcia-Granda, Santiago,Ortiz, Fernando Lopez
, p. 537 - 540 (2008/04/05)
N-Benzyldiphenylphosphinamides are deprotonated at the NCα position diastereospecifically upon treatment with f-BuLi in diethyl ether at low temperature. The reaction of the anions with alkyl, acyl, and tin halides, aliphatic and aromatic aldehydes, and Michael acceptors allowed installation of a variety of functional groups into the benzylic arm in excellent yields. Cleavage of the P-N linkage affords 1,2-amino alcohols and α-, β-, and γ-amino acids.
Asymmetric deprotonation-substitution of N-Pop-benzylamines using [RLi/(-)-sparteine]. Enantioselective sequential reactions and synthesis of N-heterocycles
Ona-Burgos, Pascual,Fernandez, Ignacio,Roces, Laura,Torre-Fernandez, Laura,Garcia-Granda, Santiago,Lopez-Ortiz, Fernando
scheme or table, p. 3195 - 3198 (2009/05/27)
(Chemical Equation Presented) Pop-directed asymmetric deprotonation of benzylic amines using [n-BuLi/(-)-sparteine] provides an efficient method for the synthesis of chiral NCα and NC α,α′ derivatives with total selectivity with respect to competing allylic and ortho lithiation. The method described herein offers a straightforward route of accessing chiral N-Pop-protected nitrogen heterocycles.
Unprecedented asymmetric induction through configurationally stable lithium N-(α-methylbenzyl)phosphinamides. A new entry to enantiomerically pure γ-aminophosphinic acids and esters
Fernandez, Ignacio,Ruiz Gomez, Gloria,Alfonso, Ignacio,Iglesias, Maria J.,Lopez Ortiz, Fernando
, p. 5408 - 5410 (2007/10/03)
The first examples of configurationally stable N-benzyl-N-phosphinoyl carbanions are described. Their applications to the synthesis of homochiral γ-aminophosphinic acids and esters via highly enantioselective dearomatising reactions are shown. The Royal S
