Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions
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Title |
Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions
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Creator |
KOTHA, S
BRAHMACHARY, E |
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Subject |
site-specific incorporation
side-chain chemoenzymatic synthesis protected derivatives metalated isocyanides axial dissymmetry glutamic-acid methyl-ester bis-alanine alkylation |
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Description |
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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2011-07-15T00:27:38Z
2011-12-26T12:49:08Z 2011-12-27T05:34:54Z 2011-07-15T00:27:38Z 2011-12-26T12:49:08Z 2011-12-27T05:34:54Z 2000 |
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Type |
Article
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Identifier |
JOURNAL OF ORGANIC CHEMISTRY, 65(5), 1359-1365
0022-3263 http://dx.doi.org/10.1021/jo991387v http://dspace.library.iitb.ac.in/xmlui/handle/10054/4105 http://hdl.handle.net/10054/4105 |
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Language |
en
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