735334-59-5Relevant academic research and scientific papers
Phosphoramidite ligands in iridium-catalyzed allvlic substitution
Polet, Damien,Alexakis, Alexandre,Tissot-Croset, Karine,Corminboeuf, Clemence,Ditrich, Klaus
, p. 3596 - 3609 (2006)
A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics was explored in detail, as was the role of the substituent in the ortho-position of the amine moiety.
Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines
Agami, Claude,Couty, Francois,Evano, Gwilherm
, p. 4639 - 4643 (2007/10/03)
The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure β-amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the β-amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses.
