Organic Letters 2006-10-12

New zinc(II)-based catalyst for asymmetric azomethine ylide cycloaddition reactions.

Ozdemir Dogan, Hasan Koyuncu, Philip Garner, Adnan Bulut, Wiley J Youngs, Matthew Panzner

Index: Org. Lett. 8 , 4687, (2006)

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Abstract

[reaction: see text] A new chiral aziridino alcohol ligand for zinc(II)-catalyzed azomethine ylide cycloadditions is described. In the presence of this catalyst, N-arylidene glycine methyl esters react with a variety of dipolarophiles to give substituted pyrrolidines in very good to excellent chemical yields and up to 95% ee. The absolute sense of asymmetric induction appears to be dipolarophile-dependent.