17118-74-0Relevant articles and documents
A single-step synthesis of xyridins A and B, metabolites from Xyris indica
Saeed, Aamer
, p. 967 - 972 (2005)
A facile single-step synthesis of the title isocoumarins isolated from Xyris indica has been elaborated. Condensation of butanoyl chloride and 2-oxobutanoyl chloride with 3,4-methylenedioxyhomophthalic acid afforded xyridin A and xyridin B, respectively. Xyridin A was saponified to the corresponding keto acid, which on reduction gave the (±)-3,4-dihydro-6,7- methylenedioxy-3-propylisocoumarin in which diastereotopy of the methylenic protons around the stereogenic center was observed. A mass fragmentation mechanism for xyridins has also been suggested.
Exploiting the Reactivity of 1,2-Ketoamides: Enantioselective Synthesis of Functionalized Pyrrolidines and Pyrrolo-1,4-benzodiazepine-2,5-diones
Acosta, Paola,Becerra, Diana,Goudedranche, Sébastien,Quiroga, Jairo,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean
, p. 1591 - 1595 (2015)
A new strategy for the synthesis of optically active pyrrolo[1,4]benzodiazepine-2,5-diones has been developed. The approach is based on an initial Michael addition of functionalized 1,2-ketoamides on nitroalkenes, with a reduction-double cyclization seque
Cationic Ir/Me-BIPAM-catalyzed asymmetric intramolecular direct hydroarylation of α-ketoamides
Shirai, Tomohiko,Ito, Hajime,Yamamoto, Yasunori
supporting information, p. 2658 - 2661 (2014/03/21)
Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various types of optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities (84-98 % ee). This is realized by the use of the cationic iridium complex [Ir(cod) 2](BArF4) and the chiral O-linked bidentate phosphoramidite (R,R)-Me-BIPAM. Carbon's got a brand new bond: Asymmetric intramolecular direct hydroarylation of α-ketoamides gives various optically active 3-substituted 3-hydroxy-2-oxindoles in high yields with complete regioselectivity and high enantioselectivities. This is realized by the use of an asymmetric cationic iridium complex formed in situ (see Scheme).
A temporary-bridge strategy for enantioselective organocatalyzed synthesis of aza-seven-membered rings
Goudedranche, Sbastien,Pierrot, David,Constantieux, Thierry,Bonne, Damien,Rodriguez, Jean
supporting information, p. 15605 - 15608 (2015/01/08)
We report the first enantioselective organocatalyzed domino synthesis of azepane moieties. This temporary-bridge strategy is based on a conceptually original annulation of ambident electrophilic and 1,4-bis-nucleophilic α-ketoamides with 1,3-bis-electrophilic enals. The obtained oxygen-bridged azepanes can be selectively transformed into optically active azepanone, azepanol or azepanedione derivatives of high synthetic value. This journal is