Solvent-enhanced diastereo- and regioselectivity in the Pd(II)-catalyzed synthesis of six- and eight-membered heterocycles via cis-aminopalladation.
Arpád Balázs, Anasztázia Hetényi, Zsolt Szakonyi, Reijo Sillanpää, Ferenc Fülöp
Index: Chemistry 15(30) , 7376-81, (2009)
Full Text: HTML
Abstract
The Pd(II)-catalyzed intramolecular oxidative cyclization of tosyl-protected cis- and trans-N-allyl-2-aminocyclohexanecarboxamides was examined, and efficient syntheses of cyclohexane-fused pyrimidin-4-ones and 1,5-diazocin-6-ones were developed. In the course of the research, a marked solvent effect was observed on both the regio- and diastereoselectivity. Additionally, a novel Pd(II)-mediated domino oxidation, oxidative amination reaction was discovered. Our experimental and theoretical findings suggest that the reactions proceed via a cis-aminopalladation mechanism.
Related Compounds
Related Articles:
2010-11-01
[J. Pept. Sci. 16(11) , 613-20, (2010)]
Chiral differentiation of some cyclic beta-amino acids by kinetic and fixed ligand methods.
2010-02-01
[J. Mass Spectrom. 45(2) , 198-204, (2010)]
2012-02-06
[Inorg. Chem. 51(3) , 1386-99, (2012)]
Residue-based control of helix shape in beta-peptide oligomers.
1997-05-22
[Nature 387(6631) , 381-4, (1997)]
2005-01-19
[J. Am. Chem. Soc. 127(2) , 547-53, (2005)]