1072874-91-9Relevant academic research and scientific papers
Ruthenium-Catalyzed Asymmetric Allylic Alkylation of Isatins
Kalnmals, Christopher A.,Parkin, Sean,Ramakrishnan, Divya,Ryan, Michael C.,Smaha, Rebecca W.,Trost, Barry M.
, (2020)
A new ruthenium-based catalytic system for branched-selective asymmetric allylic alkylation is disclosed and applied to the synthesis of chiral isatin derivatives. The catalyst, which is generated in situ from commercially available CpRu(MeCN)3PF6 and a BINOL-derived phosphoramidite, is both highly active (TON up to 180) and insensitive to air and moisture. Additionally, the N-alkylated isatins accessible using this methodology are versatile building blocks that are readily transformed into chiral analogs of achiral drug molecules.
Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal
Jette, Carina I.,Tong, Z. Jaron,Hadt, Ryan G.,Stoltz, Brian M.
supporting information, p. 2033 - 2038 (2020/01/02)
Herein, we report a Cu-catalyzed enantioselective allylic alkylation using a γ-butyrolactone-derived silyl ketene acetal. Critical to the development of this work was the identification of a novel mono-picolinamide ligand with the appropriate steric and electronic properties to afford the desired products in high yield (up to 96 %) and high ee (up to 95 %). Aryl, aliphatic, and unsubstituted allylic chlorides bearing a broad range of functionality are well-tolerated. Spectroscopic studies reveal that a CuI species is likely the active catalyst, and DFT calculations suggest ligand sterics play an important role in determining Cu coordination and thus catalyst geometry.
One-pot formation of allylic chlorides from carbonyl derivatives
Fuchter, Matthew J.,Levy, Jean-Noel
supporting information; experimental part, p. 4919 - 4922 (2009/05/31)
(Chemical Equation Presented) An efficient, one-pot method for the conversion of carbonyl electrophiles to allylic chlorides has been developed, by activating magnesium alkoxides in situ using TiCl4.
