Norephedrine-derived aminoalcohol

A few of these ligands are illustrated, including the camphor-derived ligand (6.03) (which was the first one to give high enantioselectivies), the norephedrine-derived aminoalcohol (6.04), the praline-derived ligand (6.05), aminoalcohols with axial chirality such as binaphthyl (6.06) and ferrocene-based aminoalcohols such as (6.07). ... 

Itsuno has described the first enantioselective allylation of aldehydes using crosslinked polymer-supported A-sulfonylated aminoalcohols as chiral ligands [146], Polymer-supported ligands 220 and 221 were prepared by copolymerisation of the norephedrine-derived monomer 218 or D-camphor-derived 219 with styrene and divinylbenzene (DVB) in a [chiral monomer]/[styrene]/[DVB] molar ratio of 1/8/1 (Scheme 90). 

Reagents that encompass both the alcohol and the amine functional groups of a commercially available aminoalcohol are very usefirl. Ephedrine 1.61 (R = Me), pseudoephedrine 1.78, norephedrine 1.61 (R=H) and their Aralkyl and N-acyl derivatives are commonly used, [253, 290, 320-324], as are aminoalcohols 1.79. Also popular are aminoalcohols formed from the natural aminoadds (S)-alaninol... 

Optically active allylboronates bearing chiral auxiliary located at the boron atom found widespread applications in asymmetric synthesis. Enantiomerically enriched a-alkylidene-y-lactones and lactams can also be synthesized following such a synthetic approach. VUlieras et al. (41, 45] demonstrated the potential of chiral allylboronates derived from 2-phenyl-2,3-bomanediol, ephedrine, or norephedrine for this purpose. Chiral allylboronates 46a,b were obtained in a sequence of reactions involving transformation of achiral precursors 32 into the corresponding boronic acids 44 followed by their esterification with enantiomerically pure diol or 1,2-aminoalcohol 45 (Scheme 4.10). In the case of methyl-substituted derivatives 32b (R = Me), initial composition of E- and Z-isomers was transferred to the target allylboronates 46b. Importantly, the isomeric mixture was separated by means of the column chromatography. 

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