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2005
Enantioselective syntheses
O 0031
2-Aryl-5,5-bisoxazolin-2-yl[1,3]dioxanes as Solution Phase and Immobilized
for Highly Enantioselective Cyclopropanations. — Optically active bis36- 030 Ligands
oxazoline ligands (Ia) - (Id) containing a rigid dioxane ring at the bridging carbon atom
are prepared and studied in the copper-catalyzed cyclopropanation reaction of diazoacetate with styrene. It is shown that the dioxane-bearing ligands (Ic) and (Id) induce
stereoselectivity comparable to the parent dimethylbisoxazoline. Immobilization of
ligand (Id) at bromo-Wang resin leads to ligand (Ie) which shows the highest reported
enantioselectivity for this cyclopropanation reaction using a polymer-supported bisoxazoline ligand. — (KNIGHT*, J. G.; BELCHER, P. E.; Tetrahedron: Asymmetry
16 (2005) 8, 1415-1418; Sch. Nat. Sci., Univ. Newcastle, Newcastle upon Tyne
NE1 7RU, UK; Eng.) — Mischke
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