@article{comins_kuethe_miller_fevrier_brooks_2005, title={Diels-alder reactions of N-acyl-2-alkyl(aryl)-5-vinyl-2,3-dihydro-4-pyridones}, volume={70}, ISSN={["0022-3263"]}, DOI={10.1021/jo050559n}, abstractNote={Readily available N-acyl-5-vinyl-2,3-dihydro-4-pyridones undergo Diels-Alder cyclization with various dienophiles to afford novel octahydroquinolines containing synthetically useful functionality. With dihydropyridone 5 and cis-disubstituted dienophiles, the resulting cycloadducts were obtained as single diastereomers in good to excellent yield. The corresponding reaction of 5 with methyl acrylate, acrylonitrile, and phenyl vinyl sulfone showed modest preference for the endo adducts. The effect of the dihydropyridone C-2 and C-4 substituents on the degree of diastereofacial control was examined. By using this methodology, the core decahydroquinoline skeleton of gephyrotoxin was prepared in a stereocontrolled fashion. Interesting reactivity was observed with certain dienophiles leading to ring-opening of the initially formed cycloadducts. This tandem reaction provides a route to uniquely substituted beta-aminoketones, alcohols, and unnatural amino acids.}, number={13}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Kuethe, JT and Miller, TM and Fevrier, FC and Brooks, CA}, year={2005}, month={Jun}, pages={5221–5234} } @article{kuethe_brooks_comins_2003, title={Diels-Alder reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones: regio- and stereoselective synthesis of octahydroquinolines}, volume={5}, ISSN={["1523-7052"]}, DOI={10.1021/ol027308a}, abstractNote={[reaction: see text] Readily available 5-vinyldihydropyridones 2 undergo Diels-Alder cyclization with various dienophiles to afford novel octahdroquinolines. The process is highly stereoselective and provides heterocyclic products containing synthetically useful functionality.}, number={3}, journal={ORGANIC LETTERS}, author={Kuethe, JT and Brooks, CA and Comins, DL}, year={2003}, month={Feb}, pages={321–323} } @article{comins_brooks_ingalls_2001, title={Reduction of N-acyl-2,3-dihydro-4-pyridones to N-acyl-4-piperidones using zinc/acetic acid}, volume={66}, ISSN={["0022-3263"]}, DOI={10.1021/jo001609l}, abstractNote={ADVERTISEMENT RETURN TO ISSUEPREVNoteNEXTReduction of N-Acyl-2,3-dihydro-4-pyridones to N-Acyl-4-piperidones Using Zinc/Acetic AcidDaniel L. Comins, Clinton A. Brooks, and Charles L. IngallsView Author Information Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204 [email protected]Cite this: J. Org. Chem. 2001, 66, 6, 2181–2182Publication Date (Web):February 23, 2001Publication History Received13 November 2000Published online23 February 2001Published inissue 1 March 2001https://doi.org/10.1021/jo001609lCopyright © 2001 American Chemical SocietyRIGHTS & PERMISSIONSArticle Views1185Altmetric-Citations23LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. 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Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit Read OnlinePDF (26 KB) Get e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information SUBJECTS:Catalytic reactions,Redox reactions,Transfer reactions,Zinc Get e-Alerts}, number={6}, journal={JOURNAL OF ORGANIC CHEMISTRY}, author={Comins, DL and Brooks, CA and Ingalls, CL}, year={2001}, month={Mar}, pages={2181–2182} } @article{brooks_comins_2000, title={Asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid}, volume={41}, ISSN={["0040-4039"]}, DOI={10.1016/s0040-4039(00)00460-3}, abstractNote={An asymmetric synthesis of (2S,4R)-4-hydroxypipecolic acid was accomplished in eight steps and 31% overall yield.}, number={19}, journal={TETRAHEDRON LETTERS}, author={Brooks, CA and Comins, DL}, year={2000}, month={May}, pages={3551–3553} } @article{comins_brooks_al-awar_goehring_1999, title={IMDA/retro-Mannich approach to cis-perhydroquinoline Lycopodium alkaloids: Asymmetric synthesis of (+)-luciduline}, volume={1}, ISSN={["1523-7060"]}, DOI={10.1021/ol990028j}, abstractNote={[formula: see text] The first chiral auxiliary mediated asymmetric synthesis of the naturally occurring Lycopodium alkaloid (+)-luciduline has been accomplished. Key steps include an IMDA reaction of a chiral dihydropyridine, a subsequent retro-Mannich ring opening, and a novel cationic reductive cyclization reaction.}, number={2}, journal={ORGANIC LETTERS}, author={Comins, DL and Brooks, CA and Al-awar, RS and Goehring, RR}, year={1999}, month={Jul}, pages={229–231} }