59983-38-9Relevant academic research and scientific papers
Asymmetric Synthesis of Ketones by SmI2-Mediated Allylation or Benzylation of Ketenes Followed by Enantioselective Protonation
Takeuchi, Seiji,Miyoshi, Norikazu,Ohgo, Yoshiaki
, p. 551 - 554 (2007/10/02)
SmI2-mediated allylation or benzylation of alkylarylketenes followed by enantioselective protonation with α,α'-di-o-xylenedioxide gave the corresponding ketones in 61-91percentee.
An Asymmetric Synthesis of Acyclic and Macrocyclic α-Alkyl Ketones. The Role of (E)- and (Z)-Lithioenamines
Meyers, A. I.,Williams, Donald R.,White, Steven,Erickson, Gary W.
, p. 3088 - 3093 (2007/10/02)
Metalation and alkylation of chiral imines derived from C10, C12, and C15 cyclic ketones gave, under kinetic metalation conditions, 2-alkylcycloalkanones of absolute configuration opposite to that formed from thermodynamic metalation.Thus, (S)-(-)-2-methylcyclododecanone is formed kinetically in 60percent ee, whereas (R)-(+)-methylcyclododecanone is reached in 80percent ee under thermodynamic conditions.In a similar fashion, acyclic ketones 20, via their chiral imines 17, are alkylated enantioselectively under both kinetic and thermodynamic modes.The kinetic metalation gives exclusively the (Z)-lithioenamines (19), while reflux of this lithio anion gives only the (E)-lithioenamine (19).Chiral α-substituted ketones are produced in 18-97percent ee.
