A catalytic asymmetric synthesis of 5,5-dimethylproline

Elaridi, Jomana; Jackson, W. Roy; Robinson, Andrea J.

A catalytic asymmetric synthesis of 5,5-dimethylproline

Elaridi, Jomana; Jackson, W. Roy; Robinson, Andrea J.

URI: http://hdl.handle.net/10725/2869

URL: http://www.sciencedirect.com/science/article/pii/S0957416605003411

DOI: http://dx.doi.org/10.1016/j.tetasy.2005.05.003

Date: 2015-12-22

Abstract:

The methyl ester derivative of commercially available N-acetyl-allylglycine readily undergoes cross-metathesis with 2-methylbut-2-ene and ruthenium–alkylidene catalyst to afford the prenylglycine derivative. Acid-catalysed cyclisation then affords 5,5-dimethylproline in near quantitative yield and enantioselectivity.

Citation:

Elaridi, J., Jackson, W. R., & Robinson, A. J. (2005). A catalytic asymmetric synthesis of 5, 5-dimethylproline. Tetrahedron: Asymmetry, 16(11), 2025-2029.