Selective Reductions of Cyclic 1,3-Diesters Using SmI2 and H2O | Zendy

Giuditta Guazzelli | Zendy; Sara De Grazia | Zendy; Karl D. Collins | Zendy; Hiroshi Matsubara | Zendy; Malcolm Spain | Zendy; David J. Procter | Zendy

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Selective Reductions of Cyclic 1,3-Diesters Using SmI₂ and H₂O

Author(s) -

Giuditta Guazzelli,

Sara De Grazia,

Karl D. Collins,

Hiroshi Matsubara,

Malcolm Spain,

David J. Procter

Publication year - 2009

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/ja901715d

Subject(s) - chemistry , intramolecular force , anomer , selectivity , reagent , medicinal chemistry , electron transfer , selective reduction , radical , reduction (mathematics) , carbonyl group , stereochemistry , organic chemistry , catalysis , geometry , mathematics

SmI(2)-H(2)O 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. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron transfer to the ester carbonyl and the anomeric stabilization of the resulting radical-anion intermediate. Radicals formed by one-electron reduction of the ester carbonyl group have been exploited in intramolecular additions to alkenes.

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