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Zech A, Bach T. Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds. J Org Chem. 2018;83(6):3069-3077doi: 10.1021/acs.joc.8b00238.
Zech, A., & Bach, T. (2018). Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds. The Journal of organic chemistry, 83(6), 3069-3077. https://doi.org/10.1021/acs.joc.8b00238
Zech, Andreas, and Bach, Thorsten. "Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds." The Journal of organic chemistry vol. 83,6 (2018): 3069-3077. doi: https://doi.org/10.1021/acs.joc.8b00238
Zech A, Bach T. Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds. J Org Chem. 2018 Mar 16;83(6):3069-3077. doi: 10.1021/acs.joc.8b00238. Epub 2018 Mar 06. PMID: 29478316.
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J Org Chem. 2018 Mar 16;83(6):3069-3077. doi: 10.1021/acs.joc.8b00238. Epub 2018 Mar 06.

Photochemical Reaction Cascade from O-Pent-4-enyl-Substituted Salicylates to Complex Multifunctional Scaffolds.

The Journal of organic chemistry

Andreas Zech, Thorsten Bach

Affiliations

  1. Department Chemie and Catalysis Research Center (CRC) , Technische Universität München , Lichtenbergstrasse 4 , 85747 Garching , Germany.

PMID: 29478316 DOI: 10.1021/acs.joc.8b00238

Abstract

The arene ring of the title compounds is cleaved by a reaction cascade which is initiated by an intramolecular ortho photocycloaddition reaction. Tricyclic products were obtained in a highly regio- and diastereoselective fashion via a cyclooctatriene intermediate. The facial diastereoselectivity exerted by a stereogenic center in the tether is moderate to good (dr = 65/35 to 82/18). Yields were acceptable (44-87%) except for a single substrate which had a geminal dimethyl substitution in the tether and which gave the respective product in only 14% yield. The reaction is stereoconvergent with regard to the olefin configuration ( E or Z) in agreement with a triplet mechanism of the ortho photocycloaddition step.

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