Unprecedented Alkene Transposition in Phthalate–Amino Acid Adducts

Saha, I.; Baxendale, I.R.; Baumann, M.

Abstract

A detailed account on the outcome of the thermal reaction between benzylidene phthalides and various amino acid derivatives is reported. It was discovered that the tricyclic pyrroles as previously described are not the products formed in these reactions. Instead under high-temperature conditions decarboxylated phthalamide adducts are formed within 5-10 minutes. Additionally, an unprecedented alkene transposition mechanism has been identified leading to the final products of these reactions.

Citation

Saha, I., Baxendale, I., & Baumann, M. (2018). Unprecedented Alkene Transposition in Phthalate–Amino Acid Adducts. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry, 29(20), 2648-2654. https://doi.org/10.1055/s-0037-1611294

• Journal Article Type: Article
• Acceptance Date: Oct 27, 2018
• Online Publication Date: Nov 7, 2018
• Publication Date: Dec 1, 2018
• Deposit Date: Oct 27, 2018
• Publicly Available Date: Nov 7, 2019
• Journal: Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry
• Print ISSN: 0936-5214
• Electronic ISSN: 1437-2096
• Publisher: Thieme Gruppe
• Peer Reviewed: Peer Reviewed
• Volume: 29
• Issue: 20
• Pages: 2648-2654
• DOI: https://doi.org/10.1055/s-0037-1611294
• Public URL: https://durham-repository.worktribe.com/output/1344222