Nobuaki Taniguchi

Bio: Nobuaki Taniguchi is an academic researcher from Tohoku University. The author has contributed to research in topics: Enantioselective synthesis & Michael reaction. The author has an hindex of 15, co-authored 64 publications receiving 539 citations. Previous affiliations of Nobuaki Taniguchi include Yale University & Baylor University.

Synthesis of Chiral Intermediates of Quinine Alkaloids and (+)‐ Dihydroantirhine.

Abstract: (4R,5R)-2-Ethoxy-5-ethyl-4-methoxycarbonylmeth yl-3,4,5,6-tetrahydro-2H-pyran 3, which has been enantioselectively prepared, is converted into the cis-substituted lactone 11 by treatment with propanedithiol in the presence of boron trifluoride–diethyl ether. The product 11 is converted into the synthetic intermediate 7 of quinine alkaloids and the synthetic precursor 19 of (+)-dihydroantirhine 10.

Stereoselective Alkylation of Dianions Derived from Chiral Half‐Esters of Monosubstituted Malonic Acids: Asymmetric Synthesis of α‐ Alkyl α‐Amino Acids and Key Synthetic Intermediates for Hunteria and Aspidosperma Indole Alkaloids.

Abstract: Substitution of the chiral half-esters of monosubstituted malonic acids with halides leads to the formations of mixtures of the diastereoisomeric alkyl- or benzyl-malonic half-esters. The (R)-isomers (13A and 15A–22A) were obtained from the phenylmenthyl half-ester 14 of methylmalonic acid in high diastereoisomeric excess. The same stereoisomers were also produced by reaction of the half-esters 9, 23 and 24 with methyl iodide. Their absolute configurations were determined by transforming the major products into the known α-alkyl α-amino acid derivatives 30, 33 and 35. The major product 43, prepared by allylation of the half-ester 9, was converted into two lactones 41 and 42, key intermediates for synthesis of indole alkaloids of the Hunteria and Aspidosperma types. The mechanism of the above alkylation is discussed.

Enantioselective Synthesis of 6-Oxygenated Atisine Derivative via Intramolecular Double Michael Reaction.

Abstract: An enantioselective synthesis of a 6-oxygenated atisine derivative 20 is described. The atisine skeleton 18 was stereoselectively constructed by the intramolecular double Michael reaction of the enone ester 16, derived, through the aldehyde 3, from the symmetrical ketone 4.

Domino Reactions in Organic Synthesis

Abstract: Introduction Cationic domino reactions Anionic domino reactions Radical domino reactions Pericyclic domino reactions Photochemically induced domino processes Transition metal catalysis Domino reactions initiated by oxidation or reduction Enzymes in domino reactions Multicomponent reactions Special techniques in domino reactions