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Electronic and steric effects of bis(oxazolinyl)pyridine ligands on asymmetric Diels–Alder reactions

✍ Scribed by Hong Wang; Hongming Wang; Peng Liu; Hengquan Yang; Jianliang Xiao; Can Li

Publisher
Elsevier Science
Year
2008
Tongue
English
Weight
186 KB
Volume
285
Category
Article
ISSN
1381-1169

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✦ Synopsis

A series of bis(oxazolinyl)pyridine (Pybox) ligands with different electronic and steric properties were synthesized and evaluated in the Sc(III)catalyzed asymmetric Diels-Alder reaction of alkenoyl-1,3-oxazolidin-2-ones with cyclopentadiene. The results show that electron-withdrawing groups increase the enantioselectivity, which is more significantly influenced by steric effects arising near the metal center. Up to 96% ee was obtained under mild reaction conditions when using a ligand containing the sterically bulky tBu substituent and electron-withdrawing chloride.

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