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  Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes

Liu, L., Kim, H., Xie, Y., Farès, C., Kaib, P. S. J., Goddard, R., et al. (2017). Catalytic Asymmetric [4+2]-Cycloaddition of Dienes with Aldehydes. Journal of the American Chemical Society, 139(39), 13656-13659. doi:10.1021/jacs.7b08357.

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Liu, Kim, Xie, Fares, Kaib, Goddard, List 2017.pdf (Postprint), 849KB
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Liu, Kim, Xie, Fares, Kaib, Goddard, List 2017.pdf
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 Creators:
Liu, Luping1, Author              
Kim, Hyejin1, Author              
Xie, Youwei1, Author              
Farès, Christophe2, Author              
Kaib, Philip S. J.1, Author              
Goddard, Richard3, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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 Abstract: Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Brønsted acid catalysts of the hetero-Diels–Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.

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Language(s): eng - English
 Dates: 2017-08-072017-09-252017-10-04
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/jacs.7b08357
 Degree: -

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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: 139 (39) Sequence Number: - Start / End Page: 13656 - 13659 Identifier: ISSN: 0002-7863
CoNE: https://pure.mpg.de/cone/journals/resource/954925376870