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  Confined Acid-Catalyzed Asymmetric Carbonyl-Ene Cyclization

Liu, L., Leutzsch, M., Zheng, Y., Alachraf, M. W., Thiel, W., & List, B. (2015). Confined Acid-Catalyzed Asymmetric Carbonyl-Ene Cyclization. Journal of the American Chemical Society, 137(41), 13268-13271. doi:10.1021/jacs.5b09484.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0029-2E68-3 Version Permalink: https://hdl.handle.net/21.11116/0000-0008-50A7-1
Genre: Journal Article

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 Creators:
Liu, Luping1, Author           
Leutzsch, Markus1, Author           
Zheng, Yiying2, Author           
Alachraf, M. Wasim1, Author           
Thiel, Walter2, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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 Abstract: A highly enantioselective Brønsted acid catalyzed intramolecular carbonyl–ene reaction of olefinic aldehydes has been developed. Using a confined imidodiphosphate catalyst, the reaction delivers diverse trans-3,4-disubstituted carbo- and heterocyclic five-membered rings in high yields and with good to excellent diastereo- and enantioselectivities. ESI-MS, NMR, and DFT mechanistic studies reveal that the reaction proceeds via a stepwise pathway involving a novel covalent intermediate.

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Language(s): eng - English
 Dates: 2015-09-112015-10-082015-10-21
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.5b09484
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Title: Journal of the American Chemical Society
  Other : JACS
  Abbreviation : J. Am. Chem. Soc.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 137 (41) Sequence Number: - Start / End Page: 13268 - 13271 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870