Synthesis 2016; 48(17): 2768-2780
DOI: 10.1055/s-0035-1562103
special topic
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Catalysis with Iron–Salen Complexes

Subrata Shaw
Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA   Email: james.white@oregonstate.edu
,
James D. White*
Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA   Email: james.white@oregonstate.edu
› Author Affiliations
Further Information

Publication History

Received: 13 March 2016

Accepted after revision: 04 April 2016

Publication Date:
23 May 2016 (eFirst)

Abstract

Iron(III)–salen complexes based on a chiral cis-2,5-diaminobicyclo[2.2.2]octane scaffold are used as catalysts for a variety of stereo­selective reactions. High enantio- and diastereoselectivities can be achieved with these catalysts in sulfa-Michael conjugate addition to acyclic α,β-unsaturated ketones, in regioselective δ-addition of thiols to acyclic α,β,γ,δ-unsaturated ketones, and in Conia-ene carbocyclization of alkynyl-substituted β-dicarbonyl compounds. The use of these chiral iron–salen complexes as catalysts provides a new method for conducting these three important reactions under environmentally sustainable conditions.

 
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