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Nature inspired singlet oxygen generation to access α-amino carbonyl compounds via 1,2-acyl migration

Title data

Schilling, Waldemar ; Zhang, Yu ; Sahoo, Prakash Kumar ; Sarkar, Samir Kumar ; Gandhi, Sivaraman ; Roesky, Herbert W. ; Das, Shoubhik:
Nature inspired singlet oxygen generation to access α-amino carbonyl compounds via 1,2-acyl migration.
In: Green Chemistry. Vol. 23 (2021) Issue 1 . - pp. 379-387.
ISSN 1463-9262
DOI: https://doi.org/10.1039/D0GC03555F

Abstract in another language

We have discovered chlorophyll catalyzed 1,2-acyl migration reactions to achieve α-amino carbonyl compounds directly from the enaminones. In general, singlet oxygen is generated during photosynthesis in the photosystem II center. This singlet oxygen can readily react with the unsaturated double bonds present in biomolecules. This reactivity intrigued us to apply this concept towards unsaturated enaminones and others to achieve highly valuable compounds. Indeed, this photosensitizer is very cheap, commercially available, main group metal based and provided excellent efficiency for singlet oxygen mediated chemistry by achieving high turnover number (TON) > 300 with a high turnover frequency (TOF) of 50 h−1. Finally, a combination of DFT calculations and detailed mechanistic experiments provided the exact role of the photosensitizer and clear insights into the reaction.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I > Chair Organic Chemistry I - Univ.-Prof. Dr. Das Shoubhik
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 18 Jul 2023 11:25
Last Modified: 08 Nov 2023 11:23
URI: https://eref.uni-bayreuth.de/id/eprint/86171