A concise route to β-cyclopropyl amino acids utilizing 1,2-dioxines and stabilized phosphonate nucleophiles

Date

2008

Authors

Avery, T.
Greatrex, B.
Pedersen, D.
Taylor, D.
Tiekink, E.

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Journal article

Citation

Journal of Organic Chemistry, 2008; 73(7):2633-2640

Statement of Responsibility

Avery, T.D., Greatrex, B.W., Pedersen, D.S., Taylor, D.K., Tiekink, E.R.T.

Conference Name

DOI

10.1021/jo7024256

Abstract

1,2-Dioxines react with glycine-derived phosphonate nucleophiles via a multistep cascade reaction to give β-cyclopropyl amino acid derivatives in good yield with excellent control of the cyclopropane stereocentres. The cyclopropyl ketones were oxidized to the corresponding carboxylic esters using Baeyer-Villiger conditions. Standard deprotection protocols produced a series of known β-cyclopropyl amino acids that are selective and potent agonists or antagonists of the metabotropic glutamate receptors in excellent yields.

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© 2008 American Chemical Society

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Published Version

https://doi.org/10.1021/jo7024256

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Persistent link to this record

http://hdl.handle.net/2440/47522