An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza)-alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent iodines have been compared. In particular, by using C-6 modified pyridinyl-oxazoline (Pyox) ligand and hypervalent iodine bearing an aromatic ring, an excellent enantio- and diastereoselectivity has been achieved.
Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza)-Alkenols / E.M. Beccalli, S. Giofrè, L. Molteni, D. Nava, L. Lo Presti. - In: ANGEWANDTE CHEMIE. INTERNATIONAL EDITION. - ISSN 1433-7851. - 60:40(2021 Sep 27), pp. 21723-21727. [10.1002/anie.202109312]
Enantio- and Regioselective Palladium(II)-Catalyzed Dioxygenation of (Aza)-Alkenols
E.M. Beccalli
;S. Giofrè;L. Molteni;D. Nava;L. Lo Presti
2021
Abstract
An oxidative Pd-catalyzed intra-intermolecular dioxygenation of (aza)-alkenols has been reported, with total regioselectivity. To study the stereoselectivity, different chiral ligands as well as different hypervalent iodines have been compared. In particular, by using C-6 modified pyridinyl-oxazoline (Pyox) ligand and hypervalent iodine bearing an aromatic ring, an excellent enantio- and diastereoselectivity has been achieved.
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