Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids
A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's...
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| Published in | Tetrahedron Vol. 53; no. 38; pp. 12867 - 12874 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
22.09.1997
Elsevier |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields the corresponding γ-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. |
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| AbstractList | A facile stereoselective method for the synthesis of gamma-substituted, gamma-amino acids from alpha-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of alpha-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields, the corresponding gamma-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. (C) 1997 Elsevier Science Ltd. A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete reduction of the keto functionality of α-amino acyl Meldrum's acid by sodium acetoxyborohydride. The resulting amino alkyl Meldrum's acid undergoes thermal decarboxylative ring closure to a 5-substituted pyrrolidinone which yields the corresponding γ-amino acid after basic hydrolysis. The overall yield of the procedure ranges from 40 to 65%. |
| Author | Majerová, Eva Majer, Pavel Smrcina, Martin Eissenstat, Michael A. Guerassina, Tatiana A. |
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| Keywords | SODIUM INHIBITION PEPSTATIN ANALOGS GLUTAMATE PEPSIN CYTOCHALASAN SYNTHESIS DERIVATIVES |
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| Snippet | A facile stereoselective method for the synthesis of γ-substituted, γ-amino acids from α-amino acids was developed. The key step of the procedure is complete... A facile stereoselective method for the synthesis of gamma-substituted, gamma-amino acids from alpha-amino acids was developed. The key step of the procedure... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Facile stereoselective synthesis of γ-substituted γ-amino acids from the corresponding α-amino acids |
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