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N-Alkenyl and N-alkoxymethyl lactams are impervious to many reagents and are useful protecting groups for lactams. Conversion to the corresponding 2-ethoxy iminium salt and hydrolysis in neutral water removes the protecting group. Mild basification regenerates the lactam.

N-Alkenyl- and N-alkoxymethyllactams are readily prepared from the corresponding lactam, and reaction with triethyloxonium tetrafluoroborate generates an 2-ethoxyiminium salt. Hydrolysis in neutral water gives the ethyl ester of 4-amino-butanoic acid (GABA) (or another omega-amino ester), an aldehyde and, in the case of the alkoxymethyl derivatives, an alcohol. The hydrolysis step requires participation of an enamine or N-alkoxymethyl moiety in a proton exchange reaction prior to fragmentation of the ring. The reaction shows a steric effect at the 'enamine' or N-alkoxymethyl terminus and some dependence on the size of the ring. The alkoxymethyl derivatives hydrolyze much slower than the alkenyllactam derivatives.

ChemInformVolume 21, Issue 7 Preparative Organic Chemistry ChemInform Abstract: Ethyl N-Dienylpyroglutamates: Novel Asymmetric Dienes. R. F. MENEZES, R. F. MENEZES Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorC. A. ZEZZA, C. A. ZEZZA Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorJ. SHEU, J. SHEU Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorM. B. SMITH, M. B. SMITH Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this author R. F. MENEZES, R. F. MENEZES Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorC. A. ZEZZA, C. A. ZEZZA Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorJ. SHEU, J. SHEU Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorM. B. SMITH, M. B. SMITH Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this author First published: February 13, 1990 https://doi.org/10.1002/chin.199007105Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat No abstract is available for this article. References R. F. MENEZES, C. A. ZEZZA, J. SHEU, M. B. SMITH, Ethyl N-Dienylpyroglutamates: Novel Asymmetric Dienes., Tetrahedron Lett., 1989, 30, 3295–3298. DOI: 10.1016/S0040-4039(00)99225-6; 10.1016/S0040-4039(00)99225-6 CASWeb of Science®Google Scholar Volume21, Issue7February 13, 1990 ReferencesRelatedInformation

(1989). CYCLZATION OF ω-HALONITRILES WITH ORGANOLITHIUMS. Organic Preparations and Procedures International: Vol. 21, No. 3, pp. 297-301.

Conversion of L-glutamic acid to S-ethyl pyroglutamate allows reaction with α,β-unsaturated aldehydes to give the N-dienyl derivative. The resulting dienyl pyroglutamates are new asymmetric dienes which show excellent diastereoselectivity in the Diels-Alder reaction with electron deficient alkenes.

ChemInformVolume 20, Issue 46 Heterocyclic Compounds ChemInform Abstract: Cyclization of ω-Halo Nitriles with Organolithiums. V. GALLULO, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorL. DIMAS, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorC. A. ZEZZA, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorM. B. SMITH, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this author V. GALLULO, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorL. DIMAS, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorC. A. ZEZZA, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this authorM. B. SMITH, Dep. Chem., Univ. Conn., Storrs, CT 06269, USASearch for more papers by this author First published: November 14, 1989 https://doi.org/10.1002/chin.198946195Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume20, Issue46November 14, 1989 RelatedInformation

Organic Mass SpectrometryVolume 23, Issue 4 p. 285-287 New Mass Spectra Electron impact study of N-alkenyl lactams Michael B. Smith, Corresponding Author Michael B. Smith Department Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USADepartment Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USASearch for more papers by this authorCharles A. Zezza, Charles A. Zezza Department Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USA Smith/Kline & French Research Fellow.Search for more papers by this author Michael B. Smith, Corresponding Author Michael B. Smith Department Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USADepartment Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USASearch for more papers by this authorCharles A. Zezza, Charles A. Zezza Department Of Chemistry, u-60, Rm 151, 215 Road, University Of Connecticut, Connecticut 06268, USA Smith/Kline & French Research Fellow.Search for more papers by this author First published: April 1988 https://doi.org/10.1002/oms.1210230413Citations: 2 AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Citing Literature Volume23, Issue4April 1988Pages 285-287 RelatedInformation

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTN-Dienyl lactams: preparation and selectivity in the Diels-Alder reactionCharles A. Zezza and Michael B. SmithCite this: J. Org. Chem. 1988, 53, 6, 1161–1167Publication Date (Print):March 1, 1988Publication History Published online1 May 2002Published inissue 1 March 1988https://pubs.acs.org/doi/10.1021/jo00241a008https://doi.org/10.1021/jo00241a008research-articleACS PublicationsRequest reuse permissionsArticle Views488Altmetric-Citations37LEARN 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. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

AbstractThe lactams (I) are coupled with the α,β‐unsaturated aldehydes (II) to produce the N‐dienyl lactams (III).

AbstractThe lactams (I) are coupled with the aldehydes (II) in the presence of p‐toluenesulfonic acid to produce the N‐alkenyl lactams (III) ‐ (V).

AbstractReaction of the alcohols (Ia) and (Ib) with the ethenyl pyrrole (II) followed by distillation yields the ethers (III).

AbstractDie Umsetzung der Bromide (I) mit den Aminen (II) führt unter Ringspaltung bzw. Solvolyse zu den Produkten (III) und (IV).

AbstractAus den Lactimethern (I) entstehen mit Organo‐Lithiumverbindungen (II) die Alkylierungsprodukte (III) bzw. (IV).