Synthesis, Inhaltsverzeichnis Synthesis 2020; 52(10): 1544-1560DOI: 10.1055/s-0039-1690826 paper © Georg Thieme Verlag Stuttgart · New YorkChelation and Stereodirecting Group Effects on Regio- and Diastereoselective Samarium(II)-Water Allylic Benzoate Reductions Authors Institutsangaben Trevor F. Stockdale Michael A. Leitch Gregory W. O’Neil∗ Department of Chemistry, Western Washington University, 516 High Street, Bellingham, WA 98225, USA eMail: oneilg@wwu.edu Artikel empfehlen Abstract Alle Artikel dieser Rubrik(opens in new window) Abstract SmI2(H2O)n reductions of allylic benzoates adjacent to a trisubstituted alkene occur in high yields with complete regioselectivity and good diastereoselectivity (up to 90:10) for substrates containing properly positioned stereodirecting- and chelating groups. The outcome of these reactions can be rationalized by ring conformation considerations of a proposed chelated organosamarium intermediate, and a mechanism involving intramolecular protonation by a samarium-bound water. Key words Key wordssamarium - reduction - diastereoselective - regioselective - chelation Volltext Referenzen References 1a Namy JL, Girard P, Kagan HB. New J. Chem. 1977; 1: 5 1b Kagan HB. Tetrahedron 2003; 59: 10351 2a Nicolaou KC, Ellery SP, Chen JS. Angew. Chem. Int. Ed. 2009; 48: 7140 2b Edmonds DJ, Johnston D, Procter DJ. Chem. Rev. 2004; 104: 3371 2c Molander GA, Harris CR. Chem. Rev. 1996; 96: 843 2d Szostak M, Spain M, Parmar D, Procter DJ. Chem. Soc. Rev. 2013; 42: 9155 2e Procter DJ, Flowers RA. II, Skrydstrup T. Organic Synthesis using Samarium Diiodide . RSC Publishing; Cambridge: 2010 2f Plesniak MP, Huang H-M, Procter DJ. Nat. Rev. Chem. 2017; 1: 0077 3a Enemærke RJ, Daasbjerg K, Skrydstrup T. Chem. 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