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Bichovski P, Haas TM, Keller M, et al. Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti(III)-catalysed reductive umpolung of simple activated alkenes. Org Biomol Chem. 2016;14(24):5673-82doi: 10.1039/c5ob02631h.
Bichovski, P., Haas, T. M., Keller, M., & Streuff, J. (2016). Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti(III)-catalysed reductive umpolung of simple activated alkenes. Organic & biomolecular chemistry, 14(24), 5673-82. https://doi.org/10.1039/c5ob02631h
Bichovski, Plamen, et al. "Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti(III)-catalysed reductive umpolung of simple activated alkenes." Organic & biomolecular chemistry vol. 14,24 (2016): 5673-82. doi: https://doi.org/10.1039/c5ob02631h
Bichovski P, Haas TM, Keller M, Streuff J. Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti(III)-catalysed reductive umpolung of simple activated alkenes. Org Biomol Chem. 2016 Jun 15;14(24):5673-82. doi: 10.1039/c5ob02631h. PMID: 26806535.
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Org Biomol Chem. 2016 Jun 15;14(24):5673-82. doi: 10.1039/c5ob02631h.

Direct conjugate alkylation of α,β-unsaturated carbonyls by Ti(III)-catalysed reductive umpolung of simple activated alkenes.

Organic & biomolecular chemistry

Plamen Bichovski, Thomas M Haas, Manfred Keller, Jan Streuff

Affiliations

  1. Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertsraße 21, 79104 Freiburg, Germany. [email protected].

PMID: 26806535 DOI: 10.1039/c5ob02631h

Abstract

The titanium(iii)-catalysed cross-selective reductive umpolung of Michael-acceptors represents a unique direct conjugate β-alkylation reaction. It allows the cross-selective preparation of 1,6- and 1,4-difunctionalised building blocks without the requirement of stoichiometric organometallic reagents. In this full paper, the development and scope of the titanium(iii)-catalysed cross-selective reductive umpolung of Michael-acceptors is described. Based on the observed selectivities and additional mechanistic experiments a refined mechanistic proposal is presented.

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