Stereoselective Synthesis of 3, 6-Disubstituted-3, 6-dihydropyridin-2-ones as Potential Diketopiperazine Mimetics Using Organocopper-Mediated a nti-SN2'Reactions …
A Niida, H Tanigaki, E Inokuchi, Y Sasaki…
Index: Niida, Ayumu; Tanigaki, Hiroaki; Inokuchi, Eriko; Sasaki, Yoshikazu; Oishi, Shinya; Ohno, Hiroaki; Tamamura, Hirokazu; Wang, Zixuan; Peiper, Stephen C.; Kitaura, Kazuo; Otaka, Akira; Fujii, Nobutaka Journal of Organic Chemistry, 2006 , vol. 71, # 10 p. 3942 - 3951
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Citation Number: 29
Abstract
Organocopper-mediated anti-SN2'reactions of γ-phosphoryloxy-α, β-unsaturated-δ-lactams were used to prepare highly functionalized diketopiperazine mimetics. The substrate phosphates 24, 32, and 47 were prepared from α-amino acid-derived allylic alcohols 10 by a sequence of reactions that included ring-closing metathesis. In the reactions of phosphates with organocopper reagents, the addition of LiCl dramatically improved anti-SN2' ...
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