Chiral Bicyclic Lactams Research Articles

ChemInform Abstract: Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Toward the Development of a General Chiral Auxiliary. Part 3. Design and Evaluation of a Novel Chiral Bicyclic Lactam (VI) for Asymmetric Aldol Condensations: Evidence for the Importance of Dipole Alignment in the Transition State.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)‐Laurene.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Complementary Selectivity in the Alkylation of Chiral Bicyclic Lactam Enolates

Complementary Selectivity in the Alkylation of Chiral Bicyclic Lactam Enolates

A Novel Asymmetric Route to the 1,3-Disubstituted Tetrahydroisoquinoline, (-)-Argemonine.

Chiral bicyclic lactam 13 was converted to the natural product (-)-argemonine 9 in six steps. This novel route to argemonine represents a general strategy for the preparation of chiral 1,3-disubstituted tetrahydroisoquinolines.

Single and Double Diastereoselection in Azomethine Ylide Cycloaddition Reactions with Unsaturated Chiral Bicyclic Lactams

Double diastereoselectivity data were analyzed to provide insight into the structural features that influence π-facial selectivity in 1,3-dipolar cycloadditions of chiral and achiral azomethine ylides to chiral, unsaturated bicyclic lactams. Three major steric contributions to the differences in stability (ΔΔG⧧) between competing cycloaddition transition states were identified. The first major set of steric interactions involve that between the dipoles and the substituents on the left hemisphere (R2) and concave faces of the bicyclic lactams. This effectively hindered both α- and β-approaches in the nonextended transition states shown in Figure 1. The second major steric interaction was provided by the nonbonded interactions (i) between the R1 angular substituent on the bicyclic lactam and the π-system of the dipole as shown in Figures 3 and 4. This interaction was shown to be very significant, causing reversal in π-facial attack of chiral and achiral dipoles when the angular substituent is changed from p...

Toward the Development of a General Chiral Auxiliary. 3. Design and Evaluation of a Novel Chiral Bicyclic Lactam for Asymmetric Aldol Condensations: Evidence for the Importance of Dipole Alignment in the Transition State

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTToward the Development of a General Chiral Auxiliary. 3. Design and Evaluation of a Novel Chiral Bicyclic Lactam for Asymmetric Aldol Condensations: Evidence for the Importance of Dipole Alignment in the Transition StateRobert K. Boeckman Jr. and Brian T. ConnellCite this: J. Am. Chem. Soc. 1995, 117, 49, 12368–12369Publication Date (Print):December 1, 1995Publication History Published online1 May 2002Published inissue 1 December 1995https://doi.org/10.1021/ja00154a053RIGHTS & PERMISSIONSArticle Views475Altmetric-Citations40LEARN 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 InReddit PDF (266 KB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information Get e-Alerts

Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene

Synthesis of Vicinal Stereogenic Tertiary and Quaternary Centers Using Chiral Bicyclic Lactams and Diastereoselective Protonation. Asymmetric Synthesis of (+)-Laurene

ChemInform Abstract: Asymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective, Concise Synthesis of Chiral 2‐Alkyl‐3,4‐ aziridinopyrrolidines.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Asymmetric Lewis Acid-Catalyzed Addition of a Ketene Dithioacetal to a Chiral Bicyclic Lactam. Formation of Cyclobutanopyrrolidinones. A New Class of GABA Derivatives

Asymmetric Lewis Acid-Catalyzed Addition of a Ketene Dithioacetal to a Chiral Bicyclic Lactam. Formation of Cyclobutanopyrrolidinones. A New Class of GABA Derivatives

Asymmetric conjugate additions to chiral bicyclic lactams. A stereoselective, concise synthesis of chiral 2-alkyl-3,4-aziridinopyrrolidines

Stereoselective, conjugate additions of primary amines to chiral α-iodo α, β-unsaturated bicyclic lactams are described. Typical yields of the resulting aziridinolactams ranged from 60–90% with facial diastereoselectivities of >98:2 in all cases. Selected optically pure aziridinobicyclic lactams were transformed, by reductive cleavage, into chiral 2-alkyl, 3, 4-aziridinopyrrolidines.

Asymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective General Synthesis of Chiral 3-Aminopyrrolidines

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAsymmetric Conjugate Additions to Chiral Bicyclic Lactams. A Stereoselective General Synthesis of Chiral 3-AminopyrrolidinesC. J. Andres, P. H. Lee, T. H. Nguyen, and A. I. MeyersCite this: J. Org. Chem. 1995, 60, 10, 3189–3193Publication Date (Print):May 1, 1995Publication History Published online1 May 2002Published inissue 1 May 1995https://doi.org/10.1021/jo00115a040RIGHTS & PERMISSIONSArticle Views172Altmetric-Citations27LEARN 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 InReddit PDF (644 KB) Get e-AlertsSupporting Info (2)»Supporting Information Supporting Information Get e-Alerts

Chiral bicyclic lactams–an asymmetric synthesis of the framework of the Lycopodium alkaloid magellanine containing all six adjacent stereogenic centres

A concise blioyclic lactam-mediated asymmetric synthesis of the titled ring system is described.

An asymmetric synthesis of novel aminocyclopropyl carboxylic acids (ACC)

Cyclopropanation of chiral bicyclic lactams 2 followed by removal of the chiral auxiliary and a Curtius rearrangement leads to the title compounds in >99% e.e.

Asymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidines

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAsymmetric conjugate additions to chiral bicyclic lactams. Synthesis of aracemic trans-2,3-disubstituted pyrrolidinesA. I. Meyers and Lawrence SnyderCite this: J. Org. Chem. 1992, 57, 14, 3814–3819Publication Date (Print):July 1, 1992Publication History Published online1 May 2002Published inissue 1 July 1992https://doi.org/10.1021/jo00040a018RIGHTS & PERMISSIONSArticle Views348Altmetric-Citations48LEARN 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 InReddit PDF (810 KB) Get e-Alerts Get e-Alerts

ChemInform Abstract: Chiral Non‐Racemic Bicyclic Lactams. Vehicles for the Construction of Natural and Unnatural Products Containing Quaternary Carbon Centers

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

A simple asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones

An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding γ-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be >98% by chiral stationary-phase HPLC

An Asymmetric Synthesis of the Takano Lactone. A Formal Synthesis of 9-(—)-Eburnamine

The lactone 2 known as a precursor to the alkaloid eburnamine 1 has been prepared via chiral bicyclic lactam 4 in 4 steps in 35% overall yield and >99% enantiomeric excess

Diastereoselective cyclopropanations of chiral bicyclic lactams leading to enantiomerically pure cyclopropanes. Application to the total synthesis of CIS-(1S, 3R)-deltamethrinic acid and R-(-)- dictyopterene C

A novel diastereoselective cyclopropanation based on readily available chiral bicylic lactams ( 1b-c, 6a-b) has provided a number of enantiomerically pure cyclopropanes. Cyclopropanations of unsaturated lactams ( 10a-h, 12-14) were performed using sulfur ylides as well as a 3+2 cycloaddition-photolysis sequence and furnished the desired cyclopropane adducts ( 16, 17, 19, 22) in fair to excellent yields. In all cases involving sulfur ylides, cyclopropanations proceeded with a high degree of exo/endo diastereoselectivity (>;90%). However, the mode of addition, exo vs endo, was found to be highly dependent on the angular substituent of the unsaturated lactam. In the case of diazoalkane cycloadditions, high regioselectivity was observed in all cases although exo/endo selectivity was governed by the diazoalkane employed. Diazoisopropane, being more reactive than diazomethane, normally led to lower diastereomeric ratios. Minor diastereomers could be readily removed by chromatography or in most cases by a single recrystallization to provide diastereomerically pure cyclopropyl bicyclic lactams ( 16, 17, 19, 22). Applications of this methodology to compounds of biological significance was exemplified by an asymmetric, total synthesis of cis-(1S, 3R)-deltamethrinic acid ( 34) and R-(-)- dictyopterene C' ( 42) in high enantiomeric purity.

A facile synthesis of chiral bicyclic lactams utilized in the formation of chiral quaternary carbon compounds

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTA facile synthesis of chiral bicyclic lactams utilized in the formation of chiral quaternary carbon compoundsA. I. Meyers, Bruce A. Lefker, Thomas J. Sowin, and Larry J. WestrumCite this: J. Org. Chem. 1989, 54, 17, 4243–4246Publication Date (Print):August 1, 1989Publication History Published online1 May 2002Published inissue 1 August 1989https://doi.org/10.1021/jo00278a053RIGHTS & PERMISSIONSArticle Views802Altmetric-Citations58LEARN 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 InReddit PDF (570 KB) Get e-Alerts Get e-Alerts