Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation |
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| Authors: | Clerici Angelo Pastori Nadia Porta Ombretta |
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| Affiliation: | Dipartimento di Chimica, Materiali e Ingegneria Chimica Giulio Natta, Politecnico di Milano, Sezione Chimica, Via Mancinelli 7, 20131 Milano, Italy. |
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| Abstract: | [reaction: see text] Methyl mandelate undergoes quantitative oxidative homocoupling on treatment with TiCl4/amine at room temperature. In the presence of ArCHO, quantitative syn-diastereoselective aldol condensation takes over the dimerization, whereas exclusive Mannich-type syn-diastereoselective reaction is observed in the presence of both ArCHO and PhNH2. The subsequent reactions of the title intermediate do not depend on how it is generated. |
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