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Cited by 160

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Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins

Guo, Hao, Herdtweck, Eberhardt, Bach, Thorsten·2010·Angewandte Chemie International Edition

Abstract

Photochemistry goes acidic! In the presence of the chiral Lewis acid catalyst 2 the intramolecular [2+2] photocycloaddition of 4-(alk-4-enyl)coumarins (1) provides the corresponding products 3 with up to four stereogenic centers in a highly chemo- (84–89 % yield) and stereoselective fashion. For R=H, enantioselectivities up to 82 % ee are possible with 50 mol % catalyst 2 and up to 78 % ee with only 20 mol % of catalyst 2.

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Metadata

Authors
Guo, H., Herdtweck, E., & Bach, T.
Venue
Angewandte Chemie International Edition
Publisher
Wiley
Published
2010-09-10
Volume
49
Issue
42
Pages
7782-7785
ISSN
  • 1433-7851 (ISSN-L)
  • 1521-3773
OpenAlex
W2069931068
Cited by
160
References
2
FWCI
2.05
Type
journal article
Language
en
Open access
closed

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CoChat. (2026). Citation check: Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins. https://app.cochat.ai/papers/10.1002/anie.201003619
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Guo, H., Herdtweck, E., & Bach, T. (2010). Enantioselective Lewis Acid Catalysis in Intramolecular [2+2] Photocycloaddition Reactions of Coumarins. Angewandte Chemie International Edition. https://doi.org/10.1002/anie.201003619

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Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.