Article
Inverse-electron Demand Diels Alder Reactions Between Glycals and Tetrazines
Carbohydrate Research
(2022)
Abstract
The inverse-electron demand Diels Alder reaction (IEDDA) of substituted tetrazines with 2,3-unsaturated sugars (glycals) has been investigated to prepare novel carbohydrate-based heterocycles. The cycloaddition reactions occurred in moderate to good, isolated yields and gave acyclic, C-linked pyranose diazines as the major products (33–90%). The effects of variations in sugars, sugar protecting groups, and reaction solvents on the yields and products obtained in these reactions were studied. Lower yields of adducts were isolated for TBDMS-protected glucals and for 4,6-O-benzylidene protected glucals. When unprotected sugars were used, the reactions failed to give the desired cycloadducts. A range of substituted tetrazines were also evaluated in these reactions. For comparison, HOMO-[LUMO + 1] gaps for glycal-tetrazine pairs were calculated using Density Functional (DFT) calculations at the B3LYP/631G+ level.
Keywords
- Glycal,
- Tetrazine,
- IEDDA cycloaddition,
- Pyridazine,
- HOMO-[LUMO + 1] gaps
Disciplines
Publication Date
September, 2022
DOI
10.1016/j.carres.2022.108623
Publisher Statement
Dedicated to the memory of Professor Bert Fraser Reid for his accomplishments in the chemistry of glycals.
Citation Information
Cecilia H. Marzabadi, Stephen Kelty and Alexandra Altamura. "Inverse-electron Demand Diels Alder Reactions Between Glycals and Tetrazines" Carbohydrate Research Vol. 519 (2022) p. 108623 ISSN: 0008-6215 Available at: http://works.bepress.com/stephen_kelty/17/