Preparation of enantiopure 1,4-amino alcohols derived from [3]ferrocenophanes: use in the asymmetric addition of diethylzinc to benzaldehyde

Add time:08/05/2019    Source:sciencedirect.com

A series of enantiopure 1,4-amino alcohols with a [3]ferrocenophane backbone have been synthesized. Candida rugosa lipases were used in a key step allowing the resolution of amino alcohol (1S,Rp)-1. Two other amino alcohols (1S,2S,Rp)-2 and (1S,2S,Rp)-3 were prepared starting from (1S,Rp)-1. The new ligands have been used in the asymmetric ethylation of benzaldehyde by diethylzinc and gave good catalytic properties. One of these ligands was particularly efficient, while the yield of the catalytic test reaction was near to 100% and the enantiomeric excess was about 80%. All the ligands directed the catalytic process towards the same (1R)-1-phenylpropanol.

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