Journal article
Aromatic N-heterocycles in Mn-mediated radical additions to N-acylhydrazones
Tetrahedron letters, Vol.61(27), p.152058
07/02/2020
DOI: 10.1016/j.tetlet.2020.152058
Abstract
[Display omitted]
•Radical additions to N-acylhydrazones are compatible with aromatic heterocycles.•Yields improve with increased Lewis acid stoichiometry and lower concentration.•Radical addition to a substrate containing a thiazole affords a tubuvaline precursor.
Manganese-mediated radical addition reactions to chiral N-acylhydrazones produces amines with excellent stereocontrol, but prior work showed an incompatibility with aromatic N-heterocycles. Control reactions with various aromatic heterocycles as additives led to modified reaction conditions that permit improved radical additions to N-acylhydrazones in the presence of heteroaromatic compounds. The method was applied to a revised approach to tubuvaline utilizing radical addition to a chiral N-acylhydrazone bearing a thiazole moiety.
Details
- Title: Subtitle
- Aromatic N-heterocycles in Mn-mediated radical additions to N-acylhydrazones
- Creators
- Manshu LiLevi GoffGregory K Friestad
- Resource Type
- Journal article
- Publication Details
- Tetrahedron letters, Vol.61(27), p.152058
- Publisher
- Elsevier Ltd
- DOI
- 10.1016/j.tetlet.2020.152058
- ISSN
- 0040-4039
- eISSN
- 1873-3581
- Language
- English
- Date published
- 07/02/2020
- Academic Unit
- Chemistry
- Record Identifier
- 9984216672802771
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