138797-05-4Relevant academic research and scientific papers
dl-Selective reductive coupling/Dieckmann condensation sequence of α,β-unsaturated amides with samarium(II) iodide/HMPA. Synthesis of a new ligand, trans-1,2-cyclopentanediyl-2,2'-biphenol
Kanemasa, Shuji,Yamamoto, Hidetoshi,Kobayashi, Shigeru
, p. 8505 - 8506 (1996)
By action of SmI2-HMPA in THF, the N,N-dimethyl derivatives of (E)-α,β-unsaturated amides produce the 1,2-trans-2,3-trans stereoisomers of 2,3-disubstituted 5-oxo-1-cyclopentane-carboxamides via a highly dl-selective reductive coupling followed by Dieckmann condensation. Water-d2 is an effective quenching agent. This reaction is successfully applied to the synthesis of trans-1,2-cyclopentanediyl-2,2'-biphenol, which is a new C2-symmetric chiral ligand.
A FACILE REDUCTIVE DIMERIZATION OF CONJUGATED ACID DERIVATIVES WITH SAMARIUM DIIODIDE
Inanaga, Junji,Handa, Yuich,Tabuchi, Takanori,Otsubo, Kenji,Yamaguchi, Masaru,Hanamoto, Takeshi
, p. 6557 - 6558 (2007/10/02)
Conjugated esters were instantaneously hydrodimerized at room temperature by use of the reduction system, SmI2-THF-HMPA, in the presence of proton sources.A perfect stereoselection was realized in the reaction of N,N-dibenzyl crotonamide.
