104870-80-6Relevant articles and documents
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.
Synthesis and characterization of all stereoisomers of 8-phenylmenthol
Fernandez, Franco,Garcia-Mera, Xerardo,Lopez, Carmen,Rodriguez, Gonzalo,Rodriguez-Borges, Jose Enrique
, p. 4805 - 4815 (2007/10/03)
New, improved and/or specific syntheses of the diastereoisomers of (-)-8-phenylmenthol are described. The configurations of these products, usable as chiral auxiliaries, were confirmed by X-ray diffractometry of their 3,5-dinitrobenzoates.
PREPARATION OF THREE DIASTEREOISOMERS OF 2-(1-METHYL-1-PHENYLETHYL)-5-METHYLCYCLOHEXAN-1-OL FROM (R)-(+)-PULEGONE
Cervinka, Otakar,Svatos, Ales,Masojidkova, Milena
, p. 491 - 498 (2007/10/02)
New isolation of (1R,2S,5R)-(-)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexan-1-ol ((-)-8-phenylmenthol, Ia), prepared from (R)-(+)-pulegone, is described.The method consists in the preparation of phenylcarbamate of Ia and its transesterification with ethanol.Further two diastereoisomers of (-)-8-phenylmenthol were isolated: the (1S,2R,5R)-isomer IIa and the (1R,2R,5R)-isomer IIIa.Compounds Ia, IIa and IIIa were converted into their respective glyoxylates Ic, IIc and IIIc.