425407-73-4Relevant academic research and scientific papers
Synthesis of Racemic and Enantiomerically Pure (R*,R*,R* )-Tris(α-methylbenzyl)phosphane - X-ray Crystal Structures of the Phosphane Oxides and Borane Complexes
Wyatt, Paul,Eley, Helen,Charmant, Jonathan,Daniel, Berian J.,Kantacha, Anob
, p. 4216 - 4226 (2007/10/03)
An asymmetric synthesis of C3-symmetric phosphane 1 has been achieved. Two of the α-methylbenzyl groups were introduced as nucleophiles (using an α-methylbenzyl Grignard reagent), and asymmetry was introduced by resolution using (R)-α-methylbenzylamine. The final α-methylbenzyl group was introduced as an electrophile (α-methylbenzyl iodide) in a modestly selective reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
The Stereochemical Course of Migration from Phosphorus to Nitrogen in the Photo-Curtius Rearrangement of Phosphinic Azides (Harger Reaction)
Denmark, Scott E.,Dorow, Roberta L.
, p. 5 - 6 (2007/10/02)
The homochiral phosphinic azides (R,R)-1 and (S,S)-1 have been prepared in enantiomerically pure form by resolution of diastereomeric phosphinamides derived from (S)-1-phenylethylamine and (R)-phenylglycine.Irradiation of the azides in methanol induced a photo-Curtius rearrangement of phosphonamidates in which the stereogenic carbon unit migrated to a nitrogen atom.Hydrolysis of the phosphonamidates produced 1-phenylethylamine, which was 99.0percent ee and of the same configuration as the carbon unit in the starting azide (99.0percent net retention).The implication for asymmetric synthetic methodology is discussed.
