Iron-catalyzed cyclopropanation with glycine ethyl ester hydrochloride in water

Bill Morandi; Amund Dolva; E M Carreira

doi:10.1021/ol300688p

Iron-catalyzed cyclopropanation with glycine ethyl ester hydrochloride in water

Org Lett. 2012 Apr 20;14(8):2162-3. doi: 10.1021/ol300688p. Epub 2012 Apr 11.

Authors

Bill Morandi¹, Amund Dolva, E M Carreira

Affiliation

¹ Laboratory of Organic Chemistry, ETH-Zürich , HCI H335, Wolfgang-Pauli-Strasse 10, 8093 Zürich, Switzerland.

PMID: 22494353
DOI: 10.1021/ol300688p

Abstract

An iron-catalyzed cyclopropanation reaction of styrenes in aqueous media is disclosed that employs glycine ethyl ester hydrochloride in a tandem diazotization/cyclopropanation reaction. The products are accessed in good yields and good diastereoselectivity using readily available and inexpensive starting materials. Moreover, a wide range of transition metals may be used under these conditions, thus opening new opportunities for efficient carbene-transfer reactions under user-friendly conditions.