Subscribe to RSS
DOI: 10.1055/s-1990-21197
Synthesis and Diastereoselective Reactions of Optically Active Dienone-Iron Tricarbonyl Complexes. Synthesis of Tertiary α-Hydroxyaldehydes and γ-Hydroxycrotonaldehydes as Pure Enantiomers of Known Absolute Configuration
Publication History
Publication Date:
08 March 2002 (online)
The enantiomers of known absolute configuration of trans-piperylene-iron tricarbonyl 1 [tricarbonyl(1-4-η-penta-1,3-diene)iron] react without any racemization under Friedel-Crafts conditions to give 1-acyl-1,3-pentadiene-iron tricarbonyl complexes. These are stereospecifically converted by alkyllithium reagents into complexes of tertiary alcohols, isolated as single diastereomers. After decomplexation and total or partial reductive ozonolysis, tertiary α-hydroxyaldehydes 5 or the vinylogous γ-hydroxycrotonaldehydes 6 of known absolute configuration and high optical purity are obtained in high overall yield (ca. 70 %). Starting from one piperylene complex enantiomer, both enantiomers of the final alcohol can be obtained by permutation of the order of Friedel-Crafts versus organo-lithium reactions.