708277-00-3Relevant academic research and scientific papers
Preferential formation of cis-4,5-dihydrooxazole derivatives via photoinduced electron transfer-initiated cyclization of N-acyl-α-dehydroarylalanine alkyl esters
Maekawa, Kei,Hishikawa, Norikazu,Kubo, Kanji,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 11267 - 11281 (2008/03/12)
The alkyl, aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in me
Selective and efficient transformation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters into 4,5-dihydrooxazole derivatives via photoinduced electron transfer
Maekawa, Kei,Sasaki, Takahiro,Kubo, Kanji,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 3663 - 3667 (2007/10/03)
The irradiation of N-(4-substituted benzoyl)-α-dehydroarylalanine alkyl esters (1) in methanol containing triethylamine (TEA) was found to quantitatively give cis- and trans-4,5-dihydrooxazole derivatives (2), which were described as being formed via electron transfer from TEA to the excited-state (E)-1 followed by kinetically-controlled cyclization of the (E)-1-derived anion radical. A product composition analysis showed that the cis-2/trans-2 composition ratio is greatly varied depending on the stereoelectronic properties of the substituents, the polarity of protic solvents and the concentration of TEA.
