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Stereoselective TiCl4-mediated aldol reactions starting from acylsilanes.

Abstract : A simple and efficient method for the prepn. of β-hydroxyacylsilanes has been developed through a TiCl4-mediated aldol reaction of acylsilanes with aldehydes. Acylsilane EtCOSiMe2Ph reacted with PhCHO giving 80:20 diastereomeric syn-anti mixt. of PhCH(OH)CHMeCOSiMe2Ph under TiCl4 catalysis. Similarly, arom. aldehydes contg. electron-withdrawing substituents, and isobutyraldehyde iPrCHO gave the hydroxyacyl silanes RCH(OH)CHMeCOSiMe2Ph with reasonable yields and high syn-selectivity. A selection of Lewis acids has been assessed, and other parameters such as solvent and temp. have been optimized. These aldol reactions occur under mild conditions and furnish a selection of β-hydroxy acylsilanes in fair-to-good yields with high syn selectivities (up to 99 %).
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01146438
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Submitted on : Tuesday, April 28, 2015 - 1:57:21 PM
Last modification on : Thursday, March 5, 2020 - 2:01:52 PM

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Gangababu Marri, J. Satyanarayana Reddy, Johal Ruiz, Saibal Das, Rene Gree. Stereoselective TiCl4-mediated aldol reactions starting from acylsilanes.. European Journal of Organic Chemistry, Wiley-VCH Verlag, 2015, 2015 (4), pp.840--846. ⟨10.1002/ejoc.201403263⟩. ⟨hal-01146438⟩

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