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Trost BM, Tracy JS. Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates. Chemistry. 2015;21(43):15108-12doi: 10.1002/chem.201502973.
Trost, B. M., & Tracy, J. S. (2015). Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates. Chemistry (Weinheim an der Bergstrasse, Germany), 21(43), 15108-12. https://doi.org/10.1002/chem.201502973
Trost, Barry M, and Tracy, Jacob S. "Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,43 (2015): 15108-12. doi: https://doi.org/10.1002/chem.201502973
Trost BM, Tracy JS. Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates. Chemistry. 2015 Oct 19;21(43):15108-12. doi: 10.1002/chem.201502973. Epub 2015 Sep 03. PMID: 26334442.
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Chemistry. 2015 Oct 19;21(43):15108-12. doi: 10.1002/chem.201502973. Epub 2015 Sep 03.

Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates.

Chemistry (Weinheim an der Bergstrasse, Germany)

Barry M Trost, Jacob S Tracy

Affiliations

  1. Department of Chemistry, Stanford University, Stanford, CA 94305 (USA). [email protected].
  2. Department of Chemistry, Stanford University, Stanford, CA 94305 (USA).

PMID: 26334442 DOI: 10.1002/chem.201502973

Abstract

The aldol reaction represents an important class of atom-economic carbon-carbon bond-forming reactions vital to modern organic synthesis. Despite the attention this reaction has received, issues related to chemo- and regioselectivity as well as reactivity of readily enolizable electrophiles remain. To help overcome these limitations, a new direct approach toward aldol products that does not rely upon carbonyl substrates is described. This approach employs room-temperature contemporaneous lanthanum/vanadium dual catalysis, whereby a vanadium-catalyzed 1,3-transposition of allenols is coupled with a lanthanum-catalyzed Meinwald rearrangement of epoxides in situ to directly form aldol products.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: aldol reaction; contemporaneous dual catalysis; lanthanum; rearrangement; vanadium

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