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Clerici A, Pastori N, Porta O. Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation. J Org Chem. 2005;70(10):4174-6doi: 10.1021/jo048279f.
Clerici, A., Pastori, N., & Porta, O. (2005). Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation. The Journal of organic chemistry, 70(10), 4174-6. https://doi.org/10.1021/jo048279f
Clerici, Angelo, et al. "Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation." The Journal of organic chemistry vol. 70,10 (2005): 4174-6. doi: https://doi.org/10.1021/jo048279f
Clerici A, Pastori N, Porta O. Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation. J Org Chem. 2005 May 13;70(10):4174-6. doi: 10.1021/jo048279f. PMID: 15876113.
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J Org Chem. 2005 May 13;70(10):4174-6. doi: 10.1021/jo048279f.

Reactivity of methyl mandelate-Ti(IV)-enediolate: oxidative homocoupling versus aldol and direct Mannich-type syn-diastereoselective condensation.

The Journal of organic chemistry

Angelo Clerici, Nadia Pastori, Ombretta Porta

Affiliations

  1. Dipartimento di Chimica, Materiali e Ingegneria Chimica Giulio Natta, Politecnico di Milano, Sezione Chimica, Via Mancinelli 7, 20131 Milano, Italy.

PMID: 15876113 DOI: 10.1021/jo048279f

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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