Remote stereocontrol by the sulfinyl group: Mukaiyama aldol reactions of (S)-2-[2-(p-tolylsulfinyl)phenyl]acetaldehyde in the asymmetric synthesis of β-hydroxyacids and 1,3-diols |
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Authors: | Jos L García Ruano M ngeles Fernndez-Ibez M Carmen Maestro |
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Institution: | aDepartamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain |
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Abstract: | (S)-2-2-(p-Tolylsulfinyl)phenyl]acetaldehyde reacts with different O-silylated ketenethioacetals in the presence of Yb(OTf)3 yielding β-hydroxythioesters in high yields and diastereoselectivities. The obtained compounds were readily transformed into β-hydroxyacids and their corresponding diols. These Mukaiyama aldol reactions are a direct evidence of the ability of the sulfinyl group to control 1,5- and 1,6-asymmetric induction processes. |
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Keywords: | Stereoselective Mukaiyama aldol reaction 1 5- and 1 6-Asymmetric induction Chiral sulfoxide Asymmetric synthesis of 3-hydroxyacids |
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