Synthesis of Bicyclic Tertiary α-Amino Acids

Synthesis of Bicyclic Tertiary α-Amino Acids

Novel bicyclic α-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derive...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 71; no. 26; pp. 9909 - 9911
Main Authors: Strachan, Jon-Paul, Whitaker, Regina C, Miller, Craig H, Bhatti, Balwinder S
Format: Journal Article
Language:English
Published: Washington, DC American Chemical Society 22-12-2006
Subjects:
Amino Acids - chemical synthesis
Amino Acids - chemistry
Bridged Bicyclo Compounds - chemical synthesis
Bridged Bicyclo Compounds - chemistry
Carboxylic Acids - chemical synthesis
Carboxylic Acids - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Molecular Structure
Organic chemistry
Preparations and properties
Stereoisomerism
Endo stereoisomer
Ether
Nitrogen heterocycle
Ligand
Exo stereoisomer
Glycine
Alkylation
Ring cleavage
Ammonium hydroxide
α-Aminoacid
Cyclization
Carboxylic acid
Cyclic compound
Aminoacid
Bicyclic compound
Chemical synthesis
Electrophile
Nicotinic acid derivatives
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Summary:Novel bicyclic α-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic α-amino acids.
Bibliography:istex:FB59B2A2246C76D74F217E7BE1411A87D6283B36
ark:/67375/TPS-FZRKBSKL-G
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo061977a