Volume 43, Issue 1 pp. 84-87
Communication

Kinetic Resolution of Epoxides by a CC Bond-Forming Reaction: Highly Enantioselective Addition of Indoles to cis, trans, and meso Aromatic Epoxides Catalyzed by [Cr(salen)] Complexes

Marco Bandini Dr.

Marco Bandini Dr.

Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi, 2 40126 Bologna, Italy, Fax: (+390) 51-2099456

Search for more papers by this author
Pier Giorgio Cozzi Prof. Dr.

Pier Giorgio Cozzi Prof. Dr.

Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi, 2 40126 Bologna, Italy, Fax: (+390) 51-2099456

Search for more papers by this author
Paolo Melchiorre Dr.

Paolo Melchiorre Dr.

Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi, 2 40126 Bologna, Italy, Fax: (+390) 51-2099456

Search for more papers by this author
Achille Umani-Ronchi Prof. Dr.

Achille Umani-Ronchi Prof. Dr.

Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi, 2 40126 Bologna, Italy, Fax: (+390) 51-2099456

Search for more papers by this author
First published: 17 December 2003
Citations: 120

We thank MIUR, Rome (FIRB funds), “Progetto Stereoselezione in Chimica Organica – Metodologie ed Applicazioni”, and the University of Bologna (funds for selected research topics) for financial support of this research.

Graphical Abstract

The high reactivity of indoles has led to a new approach for the kinetic resolution of epoxides. [Cr(salen)] efficiently catalyzes a new CC bond-forming reaction that allows the kinetic resolution of cis and trans aromatic epoxides (see scheme). By employing the same catalytic system, different indolyl derivatives were obtained in high enantiomeric excesses (up to 98 %) by asymmetric ring opening of meso-stilbene oxide.

The full text of this article hosted at iucr.org is unavailable due to technical difficulties.