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

Michel Franck-Neumann; Philippe Chemla; Daniel Martina

doi:10.1055/s-1990-21197

Synlett 1990; 1990(10): 641-642
DOI: 10.1055/s-1990-21197

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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

Michel Franck-Neumann^* , Philippe Chemla, Daniel Martina

^*Laboratoire de Chimie Organique Synthétique, Associé au CNRS, Institut de Chimie, Université Louis Pasteur, 1 rue Blaise Pascal, F-67008 Strasbourg, France

Abstract

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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.

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