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

Organic letters (2006-10-06)
Ozdemir Dogan, Hasan Koyuncu, Philip Garner, Adnan Bulut, Wiley J Youngs, Matthew Panzner
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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Glycine methyl ester hydrochloride, 99%
Sigma-Aldrich
Ferrocenecarboxaldehyde, 98%

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