Canadian Journal of Chemistry

Homoallylic ketones and pyrroles by way of copper-catalyzed cascade additions of alkyl-substituted vinyl Grignard reagents to esters

AA Dörr, WD Lubell

Index: Doerr, Aurelie A.; Lubell, William D. Canadian Journal of Chemistry, 2007 , vol. 85, # 11 p. 1006 - 1017

Full Text: HTML

Citation Number: 13

Abstract

Exploring the scope of the copper-catalyzed cascade addition of vinyl Grignard reagents to carboxylic esters, a set of substituted homoallylic ketones (γ, δ-unsaturated ketones) have been synthesized in 11%-94% yields from treatment of methyl 4-methoxybenzoate and methyl N-Boc-β-alaninate with different methyl-, dimethyl-, and phenyl-substituted vinyl Grignard reagents in the presence of catalytic amounts of CuCN in THF. The respective 2, ...

Related Articles:

Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters

[Lima, Paulo G.; Sequeira, Lucia C.; Costa, Paulo R.R. Tetrahedron Letters, 2001 , vol. 42, # 21 p. 3525 - 3527]

Ruthenium tetroxide oxidation of cyclic N-acylamines by a single layer method: formation of ω-amino acids

[Kaname, Mamoru; Yoshifuji, Shigeyuki; Sashida, Haruki Tetrahedron Letters, 2008 , vol. 49, # 17 p. 2786 - 2788]

Synthesis and biological properties of new 1β-methylcarbapenems

[Shin, Kye Jung; Yoo, Kyung Ho; Kim, Dong Jin; Park, Sang Woo; Ko, Bong Suck; Lee, Sang Joo; Huh, Jae Doo; Park, Seung Yong Bioorganic and Medicinal Chemistry Letters, 1998 , vol. 8, # 13 p. 1607 - 1612]

More Articles...