132273-98-4Relevant academic research and scientific papers
Synthesis of enantiomerically pure α-substituted propargylic amines by reaction of organoaluminum reagents with oxazolidines
Blanchet,Bonin,Micouin,Husson
, p. 6423 - 6426 (2007/10/03)
Various oxazolidines prepared in two steps from (R)-phenylglycinol react at 0 °C with dialkylalkynylalane-triethylamine complexes in the presence of trimethylaluminum in high yield and diastereoselectivity. Enantiomerically pure primary α-substituted propargylamines can be easily obtained in two steps after removal of ferrocenylmethyl protective group under smooth acidic conditions and oxidative cleavage of the chiral appendage.
Diastereoselective alkynylation of chiral non-racemic oxazolidines with mixed organoaluminum compounds
Blanchet, Jerome,Bonin, Martine,Chiaroni, Angele,Micouin, Laurent,Riche, Claude,Husson, Henri-Philippe
, p. 2935 - 2938 (2007/10/03)
A new efficient and scalable route to chiral non-racemic α-substituted propargylamines is described. The reaction pathway consists of the diastereoselective addition of mixed alkynylaluminum reagents to oxazolidines derived from R- (-)-phenylglycinol.
Asymmetric synthesis of α-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines
Maury, Catherine,Gharbaoui, Tawfik,Royer, Jacques,Husson, Henri-Philippe
, p. 3687 - 3693 (2007/10/03)
A simple and general asymmetric synthesis of α-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-α-substituted amino phosphonic acids in good overall yields and high ee (77→97%) after simple deprotection.
