Asymmetric and ‘anti'-Selective Aldolisations of Acetates and Propionates. Preliminary Communication

Article Article scientifique Article Asymmetric and ‘anti'-Selective Aldolisations of Acetates and Propionates. Preliminary Communication eng 1986-10-29 author Von Oppolzer Wolfgang 25270 author Marco Contelles José Luis 80435 1699-1703 10.1002/hlca.19860690725 0018-019X https://onlinelibrary.wiley.com/doi/10.1002/hlca.19860690725 Starting from acetates 1 and propionates 6, TiCl4-mediated addition of their silyketene acetals 2 and 7 to aldehydes gave aldols 4 and 9, respectively, with high π-face and ‘anti' differentiation (Schemes, and Tables 1 and 2). Alternation of the (E/Z)-enolate geometry led to reversed α- and β-inductions (7 → 9b, 8 → 10b). Non-destructive removal of the auxiliary yielded enantiomerically pure β -hydroxycarboxylic acids 13. Presented in part at the IASOC-II-Meeting, Ischia, May 1986. Dewey 540 36 Département de chimie organique 141 false Helvetica chimica acta 69 7 b61ed32a-a152-4107-8f55-7c7f00d1f55c Article (Published version) Restricted hlca.19860690725.pdf 270620 application/pdf restrictedAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique

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Asymmetric and ‘anti'-Selective Aldolisations of Acetates and Propionates. Preliminary Communication	Helvetica chimica acta			1986	125	0

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Marco Contelles, José Luis