期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 16, 期 33, 页码 10240-10249出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201000632
关键词
chemoselectivity; cyclization; radical reactions; reduction; samarium
资金
- AstraZeneca
- CNPq (Conselho Nacional de Desenvolvimento Cientifico e Tecnonologico)
- EC
- EPSRC
- University of Messina, Italy
- University of Manchester
- EPSRC [EP/H008691/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/H008691/1] Funding Source: researchfish
SmI2/H2O reduces cyclic 1,3-diesters to 3-hydroxyacids with no over reduction. Furthermore, the reagent system is selective for cyclic 1,3-diesters over acyclic 1,3-diesters, and esters. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes. The ketal unit and the reaction temperature have a marked impact on the diastereoselectivity of the cyclizations. Cyclization cascades are possible when two alkenes are present in the starting cyclic diester and lead to the formation of two rings and four stereocenters with excellent stereocontrol.
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