293737-30-1Relevant articles and documents
Production of optically active aromatic compounds having nitrogen atoms in a ring structure comprising
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Paragraph 0058-0059; 0062, (2017/08/02)
PROBLEM TO BE SOLVED: To provide a production method for obtaining an optically active aromatic compound having a cyclic structure including a nitrogen atom, in which a modified group can be removed while keeping a high yield and optical purity, with a high yield in a high enantioselective manner.SOLUTION: An aromatic compound described below is used as a substrate: in the aromatic compound, an amino group expressed by -NHR11 (where R11 is an arene sulfonyl group) is bonded to one of two carbon atoms constituting a benzene ring and adjoining to each other, and -R13-CHR15-C(=O)-Z (where R13 represents a methylene or an ethylene which may have a substituent, R15 represents a hydrogen atom, an alkyl group which may have a substituent, or a cycloalkyl group which may have a substituent, and Z represents a heteroaryl group which may have a substituent) is bonded to the other carbon atom. The substrate is made to react in a system to which N-spiro C2 axis asymmetric quaternary ammonium iodide and an oxidizing agent are supplied so as to obtain an aromatic compound having a cyclic structure including a nitrogen atom derived from the above amino group.
Stereoselective synthesis of optically active cyclic α- And β-amino esters through lipase-catalyzed transesterification or interesterification processes
Alatorre-Santamaria, Sergio,Gotor-Fernandez, Vicente,Gotor, Vicente
experimental part, p. 2307 - 2313 (2010/11/05)
A series of cyclic α- and β-amino esters belonging to a family of indolines and quinolines have been efficiently synthesized to study their behavior in lipase-mediated kinetic resolution reactions. The influence of the fused ring structure to the benzene ring and the position of the ester functionality relative to the amino group have been demonstrated, finding excellent values of enantiodiscrimination in the transesterification reaction of methyl indoline-3-carboxylate with n-butanol catalyzed by Candida antarctica lipase B being observed. On the other hand, low to moderate selectivities have been found when using a wide panel of lipases toward methyl indoline-2- carboxylate or 1,2,3,4-tetrahydroquinoline derivatives in alkoxycarbonylation, transesterification or interesterification reactions.
Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
Alatorre-Santamaria, Sergio,Rodriguez-Mata, Maria,Gotor-Fernandez, Vicente,de Mattos, Marcos Carlos,Sayago, Francisco J.,Jimenez, Ana I.,Cativiela, Carlos,Gotor, Vicente
, p. 1714 - 1719 (2008/12/20)
A series of α-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate.
METHOD FOR PREPARING (S)-INDOLINE-2-CARBOXYLIC ACID AND (S)-INDOLINE-2-CARBOXYLIC ACID METHYL ESTER USING HYDROLYTIC ENZYME
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Page/Page column 14, (2008/06/13)
Disclosed is a method for preparing (S)-indoline-2-carboxylic acid and (S)-indoline-2-carboxylic acid methyl ester using an inexpensive industrially available enzyme capable of assuring superior optical purity and yield. At this time, the hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7 and Acylase, whereby (S)-indoline-2-carboxylic acid and methyl ester thereof having an optical purity of at least 99%e.e. can be obtained through a simplified preparation process, thus generating economic benefits.
