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Ponomarenko MV, Grabowsky S, Pal R, et al. SF5-Enolates in Ti(IV)-Mediated Aldol Reactions. J Org Chem. 2016;81(15):6783-91doi: 10.1021/acs.joc.6b00946.
Ponomarenko, M. V., Grabowsky, S., Pal, R., Röschenthaler, G. V., & Fokin, A. A. (2016). SF5-Enolates in Ti(IV)-Mediated Aldol Reactions. The Journal of organic chemistry, 81(15), 6783-91. https://doi.org/10.1021/acs.joc.6b00946
Ponomarenko, Maksym V, et al. "SF5-Enolates in Ti(IV)-Mediated Aldol Reactions." The Journal of organic chemistry vol. 81,15 (2016): 6783-91. doi: https://doi.org/10.1021/acs.joc.6b00946
Ponomarenko MV, Grabowsky S, Pal R, Röschenthaler GV, Fokin AA. SF5-Enolates in Ti(IV)-Mediated Aldol Reactions. J Org Chem. 2016 Aug 05;81(15):6783-91. doi: 10.1021/acs.joc.6b00946. Epub 2016 Jul 18. PMID: 27384450.
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J Org Chem. 2016 Aug 05;81(15):6783-91. doi: 10.1021/acs.joc.6b00946. Epub 2016 Jul 18.

SF5-Enolates in Ti(IV)-Mediated Aldol Reactions.

The Journal of organic chemistry

Maksym V Ponomarenko, Simon Grabowsky, Rumpa Pal, Gerd-Volker Röschenthaler, Andrey A Fokin

Affiliations

  1. Department of Life Sciences and Chemistry, Jacobs University Bremen gGmbH , Campus Ring 1, 28759 Bremen, Germany.
  2. Universität Bremen , Institut für Anorganische Chemie und Kristallographie, Leobener Str. NW2, 28359 Bremen, Germany.
  3. Department of Organic Chemistry, Kiev Polytechnic Institute , pr. Pobedy 37, 03056 Kiev, Ukraine.

PMID: 27384450 DOI: 10.1021/acs.joc.6b00946

Abstract

The F···Ti bonding in the transition structures determines high trans- and syn-diastereoselectivities for aldol reactions of SF5-acetates with aldehydes in the presence of TiCl4 in the non-nucleophilic solvent CH2Cl2. Such bonding is canceled in nucleophilic solvents where opposite cis-stereochemistry is observed. The potential of thus obtained stereoisomeric SF5-aryl acrylates as dipolarophiles in the preparation of SF5-containing heterocycles is demonstrated.

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