Combinatorial synthetic design. Solution and polymer-supported synthesis of heterocycles via intramolecular aza Diels-Alder and imino alcohol cyclizations. Spaller, M., R., Thielemann, W., T., Brennan, P., E., & Bartlett, P., A. Journal of Combinatorial Chemistry, 4(5):516-522, American Chemical Society, 2002.
Paper
Website doi abstract bibtex Soln.-phase and polymer-bound cyclization reactions are presented as a method for the stereoselective prepn. of tetrahydroquinolines and tetrahydrobenzoxazepines with multiple points of variation as a potential method for combinatorial synthesis. Aldehydes connected to pendant alkenes undergo condensation with arom. amines to give iminium ions which can either react intramol. by aza-Diels-Alder cycloaddn. reactions with pendant alkenes to give fused tetrahydroquinolines such as pyrroloquinoline I or intermolecularly with amino alcs. to give fused pyrrolidinones such as II. The stepwise nature of the cyclizations allows the reactivity to be varied through the presence or absence of external nucleophiles. Salicylaldehyde-derived aldehydes, amides and esters of glyoxalic acid, and aldehydes derived from L-amino acids are used as the aldehyde components; this allows potential variability at the aldehyde, linker, and alkene moieties. Aza-Diels-Alder cycloaddn. reactions give products with up to four stereocenters; the products of cycloaddn. are racemic, even when aldehydes derived from L-amino acids are used as aldehyde substrates. Addn. of amino alcs. also gives racemic product except when D- or L-alaninol is used as the amino alc. component. The aza-Diels-Alder cycloaddn. of the aminoaldehydes is adapted and optimized for solid phase synthesis. [on SciFinder(R)]
@article{
title = {Combinatorial synthetic design. Solution and polymer-supported synthesis of heterocycles via intramolecular aza Diels-Alder and imino alcohol cyclizations},
type = {article},
year = {2002},
keywords = {Alcohols,Alcohols: chemistry,Combinatorial Chemistry Techniques,Heterocyclic Compounds,Heterocyclic Compounds: chemical synthesis,alkene contg aldehyde prepn condensation arom amin,arom amine aldehyde condensation stereoselective a,benzoxazepine stereoselective prepn,condensation alkene contg aldehyde arom amine ster,fused quinoline stereoselective prepn,potential combinatorial use fused quinoline benzox,soln solid phase aza Diels Alder cycloaddn amine a},
pages = {516-522},
volume = {4},
websites = {http://www.ncbi.nlm.nih.gov/pubmed/12217025,http://pubs.acs.org/doi/pdfplus/10.1021/cc020027%2B},
publisher = {American Chemical Society},
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created = {2015-10-07T14:20:51.000Z},
file_attached = {true},
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last_modified = {2018-09-03T10:20:45.804Z},
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notes = {<b>From Duplicate 2 (<i>Combinatorial Synthetic Design. Solution and Polymer-Supported Synthesis of Heterocycles via Intramolecular Aza Diels-Alder and Imino Alcohol Cyclizations</i> - Spaller, Mark R; Thielemann, Wolfgang T; Brennan, Paul E; Bartlett, Paul A)<br/></b><br/>CAPLUS AN 2002:608591(Journal)},
private_publication = {false},
abstract = {Soln.-phase and polymer-bound cyclization reactions are presented as a method for the stereoselective prepn. of tetrahydroquinolines and tetrahydrobenzoxazepines with multiple points of variation as a potential method for combinatorial synthesis. Aldehydes connected to pendant alkenes undergo condensation with arom. amines to give iminium ions which can either react intramol. by aza-Diels-Alder cycloaddn. reactions with pendant alkenes to give fused tetrahydroquinolines such as pyrroloquinoline I or intermolecularly with amino alcs. to give fused pyrrolidinones such as II. The stepwise nature of the cyclizations allows the reactivity to be varied through the presence or absence of external nucleophiles. Salicylaldehyde-derived aldehydes, amides and esters of glyoxalic acid, and aldehydes derived from L-amino acids are used as the aldehyde components; this allows potential variability at the aldehyde, linker, and alkene moieties. Aza-Diels-Alder cycloaddn. reactions give products with up to four stereocenters; the products of cycloaddn. are racemic, even when aldehydes derived from L-amino acids are used as aldehyde substrates. Addn. of amino alcs. also gives racemic product except when D- or L-alaninol is used as the amino alc. component. The aza-Diels-Alder cycloaddn. of the aminoaldehydes is adapted and optimized for solid phase synthesis. [on SciFinder(R)]},
bibtype = {article},
author = {Spaller, Mark R. and Thielemann, Wolfgang T. and Brennan, Paul E. and Bartlett, Paul A.},
doi = {10.1021/cc020027+},
journal = {Journal of Combinatorial Chemistry},
number = {5}
}
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