Mild and efficient boronic acid catalysis of Diels–Alder cycloadditions to 2-alkynoic acids
H Zheng, DG Hall
Index: Zheng, Hongchao; Hall, Dennis G. Tetrahedron Letters, 2010 , vol. 51, # 27 p. 3561 - 3564
Full Text: HTML
Citation Number: 36
Abstract
The concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied to the Diels–Alder cycloaddition between 2-alkynoic acids as dienophiles and various dienes. These [4+ 2] cycloadditions produce cyclohexadienyl carboxylic acids, which can be oxidized in situ to produce polysubstituted aromatic carboxylic acids. The boronic acid catalyst is suspected to provide activation by a LUMO-lowering effect of the ...
Related Articles:
Lithium hypochlorite-clorox as a novel oxidative mixture for methyl ketones and methyl carbinols
[Madler; Klucik; Soell; Brown; Liu; Berlin; Benbrook; Birckbichler; Nelson Organic Preparations and Procedures International, 1998 , vol. 30, # 2 p. 230 - 234]
Rhodium (I)-catalyzed carboxylation of aryl-and alkenylboronic esters with CO2
[Ukai, Kazutoshi; Aoki, Masao; Takaya, Jun; Iwasawa, Nobuharu Journal of the American Chemical Society, 2006 , vol. 128, # 27 p. 8706 - 8707]
[Choudary, Boyapati M.; Prasad, Annavajhula Durga; Bhuma, Vendantam; Swapna, Vinukonda Journal of Organic Chemistry, 1992 , vol. 57, # 22 p. 5841 - 5844]
An efficient approach for the deprotection of esters using ionic liquid as nucleophile
[Wei, Benmei; Zhang, Zhiyong; Dai, Zhiqun; Guan, Jintao Asian Journal of Chemistry, 2013 , vol. 25, # 11 p. 6404 - 6406]
[Advanced Synthesis and Catalysis, , vol. 343, # 2 p. 220 - 225]