41013-42-7Relevant academic research and scientific papers
De novo synthesis of tamiflu via a catalytic asymmetric ring-opening of meso-aziridines with TMSN3
Fukuta, Yuhei,Mita, Tsuyoshi,Fukuda, Nobuhisa,Kanai, Motomu,Shibasaki, Masakatsu
, p. 6312 - 6313 (2006)
An asymmetric ring-opening reaction of meso-aziridines with TMSN3 was developed using a catalyst prepared from Y(OiPr)3 and chiral ligand 2 in a 1:2 ratio. Excellent enantioselectivity was realized from a wide range of substrates with a practical catalyst loading. The products were efficiently converted to enantiomerically enriched 1,2-diamines, which are versatile chiral building blocks for pharmaceuticals and chiral ligands. This reaction was applied to a catalytic asymmetric synthesis of Tamiflu, a very important anti-influenza drug containing a chiral 1,2-diamino functionality. Copyright
Stereoselective Grignard reactions to α-amino nitrones. Synthesis of optically active α-aminohydroxylamines and 1,2-diamines
Merino, Pedro,Lanaspa, Ana,Merchan, Francisco L.,Tejero, Tomas
, p. 2381 - 2401 (2007/10/03)
α-Aminohydroxylamines are formed stereoselectively from the nucleophilic addition of phenylmagnesium bromide to α-amino nitrones. In contrast, the addition of methylmagnesium bromide occurs in a stereorandom fashion. Nevertheless it is possible to achieve a complete syn selectivity by diprotecting the α-amino group in the starting nitrone. Hydrogenation of the obtained α-amino hydroxylamines followed by deprotection of the tert-butoxycarbonyl group affords optically active 1,2-diamines.
