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Selective Reductions of Cyclic 1,3‐Diesters by Using SmI 2 and H 2 O
Author(s) -
Collins Karl D.,
Oliveira Juliana M.,
Guazzelli Giuditta,
Sautier Brice,
De Grazia Sara,
Matsubara Hiroshi,
Helliwell Madeleine,
Procter David J.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201000632
Subject(s) - chemistry , reagent , stereocenter , intramolecular force , medicinal chemistry , radical , reduction (mathematics) , selective reduction , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , 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. 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.