Bulletin of the Chemical Society of Japan p. 681 - 687 (2000)
Update date:2022-08-03
Topics:
Kanemasa
Adachi
Yamamoto
Wada
Enantiopure 2-amino-3,3-diphenyl-1-propanol was synthesized by the hidantoin route starting from diphenyl-acetaldehyde followed by subsequent functional group transformations and optical resolution by a chiral HPLC. The amino alcohol can be converted into two new chiral ligands: 4,4'-bis(diphenylmethyl)-2,2'-bioxazoline and 2,2'-isopropylidenebis(4-diphenylmethyloxazoline), and further to complexes with copper(II) trifluoromethanesulfonate and nickel(II) perchlorate hexahydrate. The nickel(II) aqua complex obtained from the bisoxazoline effectively catalyzed the Diels-Alder reactions of cyclopentadiene with 3-acryloyl-2-oxazolidinone in high endo-selectivities and moderate enantioselectivities via a square planar transition structure.
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