ChemInform Abstract: A Highly Diastereoselective and Enantioselective Ti(OTos)2-TADDOLate- Catalyzed 1,3-Dipolar Cycloaddition Reaction of Alkenes with Nitrones.
Abstract
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ChemInform Abstract
It is shown that the tosylate groups at the Ti atom of TTT is of utmost importance for both diastereo- and enantioselectivities of the title reaction. endo-Isoxazolidines, e.g. (IIIa) and (IIIb), with high diastereo- and enantioselectivity are obtained from N-phenyl nitrones. Reactions of N-alkyl and N-benzyl nitrones, e.g. (IIc) and (IId) give the endoisoxazolidines (IIIc) and (IIId) with the same diastereoselectivity, but the e.e. is in the range of 40-56%.
