Title

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

Document Type

Article

Publication Date

6-2002

Source Publication

Tetrahedron Letters

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

Tetrahedron Letters, Vol. 43, Issue 25 (2002), pp 4541-4543. DOI: 10.1016/S0040-4039(02)00804-3