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  Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides

Xie, Y., & List, B. (2017). Catalytic Asymmetric Intramolecular [4+2] Cycloaddition of In Situ Generated ortho-Quinone Methides. Angewandte Chemie International Edition, 56(18), 4936-4940. doi:10.1002/anie.201612149.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-002D-A5C4-F Version Permalink: https://hdl.handle.net/21.11116/0000-0008-5398-F
Genre: Journal Article

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Xie, List ACIE 2017.pdf (Postprint), 499KB
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 Creators:
Xie, Youwei1, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              

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Free keywords: asymmetric catalysis; Brønsted acids; cycloadditions; hetero-Diels-Alder reactions; organocatalysis
 Abstract: Herein, we describe the first catalytic asymmetric intramolecular [4+2] cycloaddition of in situ generated ortho-quinone methides. In the presence of a confined chiral imidodiphosphoric acid catalyst, various salicylaldehydes react with dienyl alcohols to give transient ortho-quinone methide intermediates, which undergo an intramolecular [4+2] cycloaddition to provide highly functionalized furanochromanes and pyranochromanes in excellent diastereoselectivity and enantioselectivity.

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Language(s): eng - English
 Dates: 2016-12-142017-02-172017-04-24
 Publication Status: Issued
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201612149
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 56 (18) Sequence Number: - Start / End Page: 4936 - 4940 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851