708276-89-5Relevant academic research and scientific papers
Asymmetric cyclization reactions of N-benzoyl-α-dehydroarylalanine alkyl esters via photoinduced electron transfer from achiral and chiral amines
Sasaki, Yuji,Watanabe, Haruo,Igarashi, Tetsutaro,Sakurai, Tadamitsu
, p. 1329 - 1353 (2011/07/30)
Irradiation of the title compounds [(Z)-1] having (S)-(+)-sec-butyl, (-)- menthyl, and related chiral auxiliaries in methanol and 1,2-dichloroethane containing 2-(diethylamino)ethanol afforded chiral auxiliary-substituted (4S,5S)-, (4R,5R)-, (4R,5S)-, and
Practical preparation of Z-α-(N-acetylamino)- and Z-α-(N-benzoylamino)-α,β-unsaturated acids
Jursic, Branko S.,Sagiraju, Sarada,Ancalade, Dustin K.,Clark, Traneil,Stevens, Edwin D.
, p. 1709 - 1714 (2008/02/01)
An efficient two-step synthetic procedure for the preparation of numerous variations of N-protected α,β-unsaturated α-amino acids and their corresponding esters from N-protected glycine and either aliphatic or aromatic aldehydes was developed. The reaction involved cyclization of the N-protected glycine into oxazolone, condensation with the aldehyde, and ring opening with a base. Copyright Taylor & Francis Group, LLC.
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.
