We here describe the first Cu-catalysed, diastereoselective 1,2-addition of 1,1-diborylmethane to chiral ketimines for the synthesis of quaternary stereocenters and spiro compounds. The method provides easy access to a range of chiral, highly functionalized compounds, namely oxindole-based beta,beta '-disubstituted beta-amino boronates, boron-containing peptidomimetics and six-, seven-membered spirocyclic hemiboronic esters. Such unprecedented compounds are mostly obtained in high yields and easily isolated as single diastereoisomers, paving the way to a more intense exploitation of boron-containing compounds in diversity-oriented chemistry and drug-discovery programs. Concerning stereochemistry, the application of Ellman's auxiliary strategy allows in principle to access both steric series of target compounds.

Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives [Highly diastereoselective entry to chiral oxindole-based beta-amino boronic acids and spiro derivatives] / M. Manenti, S. Gazzotti, L. Lo Presti, G. Molteni, A. Silvani. - In: ORGANIC & BIOMOLECULAR CHEMISTRY. - ISSN 1477-0520. - 19:33(2021 Sep 07), pp. 7211-7216. [10.1039/D1OB01303C]

Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives [Highly diastereoselective entry to chiral oxindole-based beta-amino boronic acids and spiro derivatives]

Manenti, Marco;Gazzotti, Stefano;Lo Presti, Leonardo;Molteni, Giorgio;Silvani, Alessandra
2021-09-07

Abstract

We here describe the first Cu-catalysed, diastereoselective 1,2-addition of 1,1-diborylmethane to chiral ketimines for the synthesis of quaternary stereocenters and spiro compounds. The method provides easy access to a range of chiral, highly functionalized compounds, namely oxindole-based beta,beta '-disubstituted beta-amino boronates, boron-containing peptidomimetics and six-, seven-membered spirocyclic hemiboronic esters. Such unprecedented compounds are mostly obtained in high yields and easily isolated as single diastereoisomers, paving the way to a more intense exploitation of boron-containing compounds in diversity-oriented chemistry and drug-discovery programs. Concerning stereochemistry, the application of Ellman's auxiliary strategy allows in principle to access both steric series of target compounds.
Settore CHIM/06 - Chimica Organica
ago-2021
ORGANIC & BIOMOLECULAR CHEMISTRY
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/864045
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