Synthesis of cyclopropanes via organoiron methodology: stereoselective preparation of cis-2-(2’-carboxycyclopropyl)glycine

Authors

Nathaniel J Wallock, Marquette UniversityFollow
William Donaldson, Marquette UniversityFollow

Document Type

Article

Language

eng

Publication Date

6-2002

Publisher

Elsevier

Source Publication

Tetrahedron Letters

Source ISSN

0040-4039

Abstract

A stereoselective route to cis-2-(2′-carboxycyclopropyl)glycine has been developed. exo-Nucleophilic addition to the (bicyclo[5.1.0]octadienyl)iron(1+) cation establishes the relative stereochemistry at the cyclopropane ring and the α-stereocenter. Subsequent removal of the metal and cleavage of the cyclic diene gave the protected target 10, which upon hydrolysis gave 1.

A stereoselective route to cis-2-(2′-carboxycyclopropyl)glycine has been developed. exo-Nucleophilic addition to the (bicyclo[5.1.0]octadienyl)iron(1+) cation establishes the relative stereochemistry at the cyclopropane ring and the α-stereocenter.

Comments

Accepted version. Tetrahedron Letters, Vol. 43, Issue 25 (2002), pp 4541-4543. DOI. © 2002 Elsevier. Used with permission.

Recommended Citation

Wallock, Nathaniel J and Donaldson, William, "Synthesis of cyclopropanes via organoiron methodology: stereoselective preparation of cis-2-(2’-carboxycyclopropyl)glycine" (2002). Chemistry Faculty Research and Publications. 68.
https://epublications.marquette.edu/chem_fac/68