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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/10054/4105

Title: Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions
Authors: KOTHA, S
BRAHMACHARY, E
Keywords: site-specific incorporation
side-chain
chemoenzymatic synthesis
protected derivatives
metalated isocyanides
axial dissymmetry
glutamic-acid
methyl-ester
bis-alanine
alkylation
Issue Date: 2000
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY, 65(5), 1359-1365
Abstract: Conformationally constrained cyclic alpha-amino acid derivatives were synthesized under solid-liquid phase-transfer catalysis conditions. This methodology involves the bis-alkylation of ethyl isocyanoacetate with various alpha,alpha'-dibromo-o-xylene derivatives [alpha,alpha'-dibromo-o-xylene 5, 2,3-bis(bromomethyl)-1,4-dimethoxybenzene 6, 1,2-bis(bromomethyl)-4,5-dibromobenzene 7, 2,3-bis(bromomethyl)naphthalene 8, 1,8-bis(bromomethyl)-naphthalene 9, 6,7-bis(bromomethyl)-2,2-dimethyl-1H-phenalene 1,3(2H)-dione 10, 2,3-bis(bromomethyl)-1,4-anthraquinone 11, 6,7-bis(bromomethyl)quinoxaline 12, 3,4-bis(bromomethyl)furan 13, 1,2,4,5-tetrakis(bromomethyl)benzene 28, and hexakis(bromomethyl)benzene 30] using potassium carbonate as a base and tetrabutylammonium hydrogensulfate as a phase-transfer catalyst to give corresponding isonitrile derivatives, which upon hydrolysis with HCl in ethanol gave amino esters. Using this method electron-deficient as well as electron-rich and halogen-substituted indan-based alpha-amino acids were prepared. The preparation of bis-indan as well as tris-indan alpha-amino esters is also described.
URI: http://dx.doi.org/10.1021/jo991387v
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4105
http://hdl.handle.net/10054/4105
ISSN: 0022-3263
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