Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

Robert S Paley; Jane M Liu; Bruce R Lichtenstein; Vanessa L Knoedler; Toby T Sanan; Drew J Adams; Jorge Fernández; Paul R Rablen

doi:10.1021/ol027306q

Simultaneous and stereoselective formation of planar and axial chiralities in enantiopure sulfinyl iron diene complexes

Org Lett. 2003 Feb 6;5(3):309-12. doi: 10.1021/ol027306q.

Authors

Robert S Paley¹, Jane M Liu, Bruce R Lichtenstein, Vanessa L Knoedler, Toby T Sanan, Drew J Adams, Jorge Fernández, Paul R Rablen

Affiliation

¹ Swarthmore College, Department of Chemistry, Swarthmore, Pennsylvania 19081, USA. rpaley1@swarthmore.edu

PMID: 12556179
DOI: 10.1021/ol027306q

Abstract

[reaction: see text] Enantiopure (1Z,3E)-1-sulfinyl dienes bearing an o-dithianylphenyl group can be prepared and complexed with (bda)Fe(CO)(3) to afford the corresponding sulfinyl diene iron(0) tricarbonyl complexes. This diastereoselective complexation introduces planar and axial chirality simultaneously, with a high degree of facial selectivity as well as atropselectivity. Dynamic kinetic resolution is likely to be the origin of the atropselectivity.