Selective reductions of cyclic 1,3-diesters by using SmI(2) and H(2)O

Chemistry : a European Journal
Karl D CollinsDavid J Procter

Abstract

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.

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Citations

Apr 28, 2012·Nature Protocols·Michal SzostakDavid J Procter
Jun 21, 2016·The Journal of Organic Chemistry·Chriss E McDonaldJustin A Cumens
Jul 2, 2016·Journal of the American Chemical Society·Tesia V ChciukRobert A Flowers
Dec 22, 2016·Organic Letters·Tesia V ChciukRobert A Flowers
Mar 2, 2018·Angewandte Chemie·Huan-Ming HuangDavid J Procter
Feb 13, 2016·Dalton Transactions : an International Journal of Inorganic Chemistry·Xuefei ZhaoLaurent Maron
Sep 1, 2011·Chemical Communications : Chem Comm·Michal SzostakDavid J Procter
Mar 1, 2012·Organic & Biomolecular Chemistry·Michal SzostakDavid J Procter
Jun 20, 2014·Chemical Communications : Chem Comm·Michal SzostakDavid J Procter
Aug 23, 2011·Chemical Communications : Chem Comm·Michal SzostakDavid J Procter
Sep 12, 2014·Chemical Communications : Chem Comm·Irem YalavacDavid J Procter
Aug 16, 2012·Angewandte Chemie·Michal Szostak, David J Procter
Mar 8, 2013·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Kovuru Gopalaiah, Henri B Kagan
Feb 11, 2011·Journal of the American Chemical Society·Dixit ParmarDavid J Procter
Apr 15, 2015·Accounts of Chemical Research·Xavier Just-Baringo, David J Procter
Apr 25, 2014·Chemical Reviews·Michal SzostakDavid J Procter
Jul 4, 2012·Journal of the American Chemical Society·Dixit ParmarDavid J Procter
Jan 26, 2012·Organic Letters·Michal SzostakDavid J Procter
Dec 1, 2011·Organic Letters·Brice SautierDavid J Procter

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