C1-Substituted N-tert-butoxycarbonyl-5-syn-tert-butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexanes as conformationally constrained β-amino acid precursors

Regioselective introduction and transformation of substituents at the C carbon of -butoxycarbonyl-5- -butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane ( ) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite...

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Published inHeterocyclic communications Vol. 22; no. 6; pp. 319 - 328
Main Authors Krow, Grant R., Gandla, Deepa, Cannon, Kevin C., Ross, Chuck W., Carroll, Patrick J.
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.12.2016
Walter de Gruyter GmbH
Subjects
Amino acids
constrained
foldamers
Hexanes
Precursors
pyrrolidine-3-carboxylic acids
β-amino acid
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Summary:Regioselective introduction and transformation of substituents at the C carbon of -butoxycarbonyl-5- -butyldimethylsilyloxymethyl-2-azabicyclo[2.1.1]hexane ( ) is described. These azabicycles are precursors to conformationally constrained β-amino acids with potential to form oligomers with definite secondary structures. Selected examples of these precursors are converted into their corresponding amino acid derivatives.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2016-0046