Journal of Organic Chemistry p. 7902 - 7907 (1994)
Update date:2022-08-11
Topics:
Akane, Noriyuki
Hatano, Tadashi
Kusui, Hiroko
Nishiyama, Yutaka
Ishii, Yasutaka
Samarium(II) species can be efficiently generated in situ from a reaction between elemental samarium and chlorotrimethylsilane (Me3SiCl)/sodium iodide (NaI) reagent or bromotrimethylsilane (Me3SiBr) in acetonitrile.The reductive coupling reaction of carbonyl compounds was achieved by the action of Sm(II) reagent thus generated from Sm/Me3SiCl/NaI or Sm/Me3SiBr to give the corresponding pinacol products in moderate to high yields.The samarium(II) reagent induced the intermolecular coupling reaction of α,β-unsaturated esters with carbonyl compounds or imines followed by intramolecular cyclization to form the corresponding γ-lactones or γ-lactams in moderate yields.The reaction of α-bromo esters with carbonyl compounds using the Sm(II) species, generated from the Sm/Me3SiX system, led to the corresponding β-hydroxy esters in 52-95percent yields.
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