74764-98-0Relevant articles and documents
Oxidative esterification, thioesterification, and amidation of aldehydes by a two-component organocatalyst system using a chiral N-heterocyclic carbene and redox-active riboflavin
Iwahana, Soichiro,Iida, Hiroki,Yashima, Eiji
, p. 8009 - 8013 (2011)
Flavin of the month! Triazolium-derived N-heterocyclic carbenes (NHCs) and a flavin catalyzed the oxidative esterification, thioesterification, and amidation of aldehydes with various alcohols, thiols, and amines, respectively, with O2 as the terminal oxidant (see scheme; R1=aryl; R2, R3=alkyl or aryl). By using a chiral NHC catalyst, the enantioselective acylation promoted the kinetic resolution of racemic alcohols and the desymmetrization of a meso-diol.
Diastereoselective photocycloaddition reactions of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furans governed by chiral auxiliaries and hydrogen bonding interactions
Maeda, Hajime,Koshio, Norihiro,Tachibana, Yuko,Chiyonobu, Kazuhiko,Konishi, Gen-ichi,Mizuno, Kazuhiko
, p. 7 - 17 (2017/09/12)
By using chiral auxiliaries and hydrogen bonding interactions, we have developed diastereoselective photocycloaddition of 2-naphthalenecarboxylates and 2,3-naphthalenedicarboxylates with furan derivatives. In photoreactions of (?)-menthyl 2-naphthalenecarboxylate with furan and 3-furanmethanol, respective maximum 48% and 40% diastereomeric excesses (d.e.) are observed. In photoreactions of di-8-phenyl-(?)-menthyl 2,3-naphthalenedicarboxylate with 3-furanmethanol, maximum 67% d.e. is obtained. Use of solvents of low polarity, low temperatures and low furan concentration leads to increased diastereoselectivities. Variable-temperature (VT) NMR and fluorescence quenching studies indicate that hydrogen bonding interactions between the carbonyl oxygen of naphthalenecarboxylic acid esters and the OH group in 3-furanmethanol take place in both the ground and excited states. The results of computational studies show that geometries of C2 symmetric naphthalenedicarboxylate reactants are important in governing the high diastereoselectivity in the photoreactions of 2,3-naphthalenedicarboxylates.
Inert-molecule-separated ion pairs. Stereochemical, 18O, and product studies
White, Emil H.,Field, Kurt W.,Hendrickson, William H.,Dzadzic, Petar,Roswell, David F.,Paik, Seunguk,Mullen, Patrick W.
, p. 8023 - 8031 (2007/10/02)
Nitrogen- and nitrous oxide-separated carbocation-carboxylate ion pairs have been prepared by five different reactions: the rearrangement of N-nitroso amides, the reaction of acid chlorides with anti-diazoates, the reaction of acid chlorides with syn-diaz
ENANTIOMER DIFFERENTIAITION IN THE PHOTOINDUCED 1,5-PHENYL SHIFT OF 3-METHYL-3-PHENYL-2(3H)-OXEPINONE UTILIZING CHIRAL SENSTIZERS
Hoshi, Nobuto,Furukawa, Yuichi,Hagiwara, Hisahiro,Uda, Hisashi,Sato, Kazuhiro
, p. 47 - 50 (2007/10/02)
Enantiomer differentiation has been observed in the initial 1,5-phenyl shift of the sensitized photorearrangement of racemic 3-methyl-3-phenyl-2(3H)-oxepinone with chiral N-(1-phenylethyl)naphthalene-carboxamides leading to optically active 4-methyl-7-exo-phenyl-2-oxabicyclohept-4-en-3-one.
PARTIAL ASYMMETRIC SYNTHESIS OF ATROPISOMERIC 1,1'-BINAPHTHYLS VIA THE ULLMANN COUPLING REACTION OF CHIRAL ALCOHOL ESTERS OF 1-BROMO-2-NAPHTHOIC ACID
Miyano, Sotaro,Tobita, Masayuki,Suzuki, Shoji,Nishikawa, Yukio,Hashimoto, Harukichi
, p. 1027 - 1030 (2007/10/02)
The Ullmann coupling of 1-bromo-2-naphthoates of C-chiral alcohols of R- and S-configuration induced axial dissymmetry of R- and S-chirality, respctively, in the newly formed 1,1'-bond of the binaphthyls; the optical yield amounted up to 13percent where the chiral alcohol was l-menthol.
