113266-44-7Relevant academic research and scientific papers
The Heck reaction under ball-milling conditions
Tullberg, Erik,Peters, Dan,Frejd, Torbj?rn
, p. 3778 - 3781 (2004)
The synthesis of unsaturated unnatural amino acids according to the Heck-Jeffery protocol using a ball-milling procedure is presented. NOE data recorded on the products confirm that the Z-isomer is formed. This type of mechano-chemistry provides an efficient, "solvent free" and reliable method for the synthesis of substituted dehydroalanines. These conditions provide patterns of reactivity complementary to conventional procedures.
Aspects of the Palladium-Catalyzed Coupling between Aryl Halides and 2-Amidoacrylates
Carlstroem, Anne-Sofie,Frejd, Torbjoern
, p. 163 - 171 (2007/10/02)
The effect of using different salts, bases, catalysts and solvents as well as protecting froups in 2-amidoacrylate derivatives (olefin component) in the Heck coupling with iodobenzene has been studied.Salt effects, resulting in increased yields, were observed in combination with either NaHCO3 or triethylamine as the base.Pd(OAc)2, PdCl2, Pd/C and hydrogen-activated Pd black could all be used as catalyst with similar results.The best solvents were DMF or acetonitrile.Olefins 1a and 1c, both carrying orthogonal protecting groups, show the most potential for further app lications in peptide synthesis. 1,2-Diodobenzene and 1,8-diiodonaphthalene did not given any coupling products and 1-bromo-2-iodobenzene gave only mono-coupling in modest yield.In fact, small amounts of either 1,2-diiodobenzene or 1,8-diiodinaphthalene inhibited the coupling in other, normally reactive, cases.In experiments stoichiometric in Pd(OAc)2 it was found that an indolecarboxylic acid derivative was formed from iodobenzene, 2-bromoiodobenzene and 1,2-diiodobenzene, suggesting that ortho-palladation of a phenyl didehydroalanine derivative is involved.
Palladium-Catalyzed Synthesis of Didehydroamino Acid Derivatives
Carlstroem, Anne-Sofie,Frejd, Torbjoern
, p. 414 - 418 (2007/10/02)
The palladium-catalyzed coupling of 2-amidoacrylates with aryl iodides under phase-transfer conditions yields aromatic (Z)-didehydroamino acid derivatives, which give various protected aromatic amino acids via catalytic hydrogenation using Pd/C or the Wil
