Diastereospecific addition of Grignard reagents to 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene-2-carboxaldehyde

The reaction of both enantiomers of 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene-2-carboxaldehyde 1 with EtMgBr and PhMgBr has been studied. It has been found that addition of a Grignard reagent to the carbonyl group of 1 proceeds diastereospecifically. The configuration of the sp 3 stereogenic cen...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2007-08, Vol.18 (15), p.1766-1768
Main Authors: Mucha, Bartosz, Kłys, Arkadiusz, Rybarczyk-Pirek, Agnieszka, Zakrzewski, Janusz
Format: Article
Language:English
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Summary:The reaction of both enantiomers of 3,3′,4,4′-tetramethyl-1,1′-diphosphaferrocene-2-carboxaldehyde 1 with EtMgBr and PhMgBr has been studied. It has been found that addition of a Grignard reagent to the carbonyl group of 1 proceeds diastereospecifically. The configuration of the sp 3 stereogenic centre formed in this reaction has been determined by single crystal X-ray diffraction and can be explained assuming exo-attack of the nucleophile on the s- cis-conformation of 1. The circular dichroism spectra of the product 1,1′-diphosphaferrocenyl alcohols are also reported and discussed.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.07.014