347384-33-2Relevant academic research and scientific papers
Stereoselective synthesis of highly enantioenriched 3-methyl-2-cyclohexen-1-ones possessing an asymmetric quaternary carbon as C-4 or C-6: a sugar template approach
Kubo, Hiroto,Kozawa, Ikuko,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 1203 - 1207 (2008/09/17)
The 1,4-addition of the enolate generated from α-methylated acetoacetate incorporated at C-4 of methyl 6-deoxy-2,3-di-O-(tert-butyldimethylsilyl)-α-d-glucopyranoside to methyl vinyl ketone, followed by aldol condensation of the resulting 1,4-addition prod
Stereoselective double alkylation of the acetoacetate ester α-carbon on a D-glucose-derived template: Application to the synthesis of enantiopure cycloalkenones bearing an asymmetric quaternary carbon
Kozawa, Ikuko,Akashi, Yoko,Takiguchi, Kumiko,Sasaki, Daisuke,Sawamoto, Daisuke,Takao, Ken-Ichi,Tadano, Kin-Ichi
, p. 399 - 402 (2007/12/27)
The previously developed D-glucose derivative, i.e., methyl 6-deoxy-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside, served as a significant stereocontrolling element for the diastereoselective alkylation of the α-carbon in its acetoacetate at C-4
Highly diastereoselective Diels-Alder reactions of acrylic esters incorporated into a variety of hexopyranosides
Nagatsuka, Takayuki,Yamaguchi, Shuhei,Totani, Kiichiro,Takao, Ken-ichi,Tadano, Kin-ichi
, p. 519 - 535 (2007/10/03)
The Diels-Alder reactions of a variety of hexopyranosides carrying an acrylic ester with cyclopentadiene were examined. Some acrylic esters provided the cycloaddition products carrying a norbornene carboxylate with a high level of diastereoselectivity. Plausible mechanisms are presented for the cases of a 4-O-acryloyl-6-deoxy-α-D-glucopyranosidic and 2-O-acryloyl-α-D-glucopyranosidic substrates. By reductive removal of the carbohydrate templates from the adducts, either 2S or 2R-enriched 5-norbornene-2-methanol were obtained.
