Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 15, Pages 7694-7713Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00575
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Funding
- CNPq
- CAPES
- TWAS
- FAPESP [14/50249-8, 15/08541-6, 13/02311-3]
- GlaxoSmithKline (GSK)
- Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [14/50249-8, 13/02311-3, 15/08541-6] Funding Source: FAPESP
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A straightforward protocol integrating a sustainable approach for the synthesis of new 2,S-trans-THF nitrile derivatives enabling an easy diversification of its side chain scaffolds is described. The reaction tolerated different aromatic and alkyl substituents, affording the corresponding 2,5-trans-THFs in high diastereoselectivity. A detailed mechanistic study using DFT calculation reveals details of the ligand-exchange step, suggesting an inner-sphere syn attack to form the 2,5-trans stereochemistry as the most likely pathway, excluding the previous cation radical intermediate. The formation of a Co-C intermediate is suggested on the basis of the homolytic cleavage to give the previously proposed free carbon radical intermediate.
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