219700-34-2Relevant academic research and scientific papers
A novel attractive interaction in the Diels-Alder reaction of N-protected pyrroles with allene-1,3-dicarboxylates
Nishide, Kiyoharu,Ichihashi, Shogo,Kimura, Hiroyuki,Katoh, Takahiro,Node, Manabu
, p. 9237 - 9240 (2001)
The endo/exo selectivities of Diels-Alder reactions of N-protected pyrroles with allene-1,3-dicarboxylates were studied under Lewis acid assisted and thermal reaction conditions. A novel attractive effect between the N-protective carbonyl group of pyrrole and the ester group of allene-1,3-dicarboxylates operates to control the selectivity in the above Diels-Alder reaction. This new attractive effect to give the exo adduct is more effective than the Alder orbital effect.
Synthesis of (-)-epibatidine and its derivatives from chiral allene-1,3-dicarboxylate esters
Kimura, Hiroyuki,Fujiwara, Toshio,Katoh, Takahiro,Nishide, Kiyoharu,Kajimoto, Tetsuya,Node, Manabu
, p. 399 - 402 (2007/10/03)
(-)-Epibatidine, an excellent candidate of non-opioidal anesthesia, was formally synthesized in short steps from di-(l)-menthyl (R)-allene-1,3- dicarboxylate that was facilely prepared as a single isomer by means of crystallization-induced asymmetric tran
New asymmetric transformation of optically active allene-1,3-dicarboxylate and its application to the formal asymmetric synthesis of (-)-epibatidine
Node, Manabu,Nishide, Kiyoharu,Fujiwara, Toshio,Ichihashi, Shogo
, p. 2363 - 2364 (2007/10/03)
A new efficient synthesis of di-(-)-L-menthyl (R)-allene-1,3-dicarboxylate [(R)-1] involving asymmetric transformation through epimerization-crystallization with the assistance of a catalytic amount of Et3N was developed; the highly endo-select
