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  A Striking Case of Enantioinversion in Gold Catalysis and Its Probable Origins

Ilg, M. K., Wolf, L. M., Mantilli, L., Farès, C., Thiel, W., & Fürstner, A. (2015). A Striking Case of Enantioinversion in Gold Catalysis and Its Probable Origins. Chemistry – A European Journal, 21(35), 12279-12284. doi:10.1002/chem.201502160.

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 Creators:
Ilg, Marina K.1, Author              
Wolf, Larry M.2, Author              
Mantilli, Luca1, Author              
Farès, Christophe3, Author              
Thiel, Walter2, Author              
Fürstner, Alois1, Author              
Affiliations:
1Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445584              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: density functional calculation; enantioinversion; gold; heterogeneouscatalysis; phosphoramidites
 Abstract: The cyclization of the hydroxy-allene 2 to the tetrahydrofuran 3 catalyzed by the gold-phosphoramidite complex 1, after ionization with an appropriate silver salt AgX, is one of the most striking cases of enantioinversion known to date. The major reason why the sense of induction can be switched from (S) to (R) solely by changing either the solvent or the temperature or the nature of the counterion X is likely found in the bias of the organogold intermediates to undergo assisted proto-deauration. Such assistance can be provided by a protic solvent, a reasonably coordinating counterion or even by a second substrate molecule itself; in this case, the reaction free energy profile gains a strong entropic component that can ultimately dictate the stereochemical course.

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Language(s): eng - English
 Dates: 2015-06-092015-07-232015-08-24
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201502160
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 21 (35) Sequence Number: - Start / End Page: 12279 - 12284 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058