Issue 16, 2006
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis of orthogonally protected trans-cyclopropane γ-amino acids via intramolecular ring closure†

David J. Fox,*a   Daniel Sejer Pedersena  and  Stuart Warrena  

* Corresponding authors

a Cambridge University, University Chemical Laboratory, Lensfield Road, Cambridge, UK
E-mail: djf34@cam.ac.uk

Abstract

The synthesis of enantiomerically-enriched trans-cyclopropane amino- and hydroxy-acids can be achieved by intramolecular ring closure in moderate to good yields. The optically active cyclopropane precursors are easily prepared in a short sequence from inexpensive, commercially available olefins and tert-butyl acetate. Several leaving groups and bases were compared for the cyclopropanation step, showing that the diphenylphosphinate and tosyl leaving groups give the best results when used in combination with either LDA or NaHMDS.

Graphical abstract: Asymmetric synthesis of orthogonally protected trans-cyclopropane γ-amino acids via intramolecular ring closure

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Article information

DOI
https://doi.org/10.1039/B606879K
Article type
Paper
Submitted
15 May 2006
Accepted
21 Jun 2006
First published
06 Jul 2006

Org. Biomol. Chem., 2006,4, 3113-3116

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Asymmetric synthesis of orthogonally protected trans-cyclopropane γ-amino acids via intramolecular ring closure

D. J. Fox, D. S. Pedersen and S. Warren, Org. Biomol. Chem., 2006, 4, 3113 DOI: 10.1039/B606879K

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