Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams

[Image: see text] Asymmetric and site-selective formal [3 + 2]-annulations of γ-alkyl-β,γ-unsaturated γ-lactams with α,β-unsaturated aldehydes have been developed. These organocatalysed transformations yield high value enantioenriched bicyclic γ-lactams with up to four new stereocenters (sometimes i...

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Autores principales: Kalaitzakis, Dimitris, Sofiadis, Manolis, Triantafyllakis, Myron, Daskalakis, Konstantinos, Vassilikogiannakis, Georgios
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2018
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822218/
https://www.ncbi.nlm.nih.gov/pubmed/29417818
http://dx.doi.org/10.1021/acs.orglett.8b00076
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author Kalaitzakis, Dimitris
Sofiadis, Manolis
Triantafyllakis, Myron
Daskalakis, Konstantinos
Vassilikogiannakis, Georgios
author_facet Kalaitzakis, Dimitris
Sofiadis, Manolis
Triantafyllakis, Myron
Daskalakis, Konstantinos
Vassilikogiannakis, Georgios
author_sort Kalaitzakis, Dimitris
collection PubMed
description [Image: see text] Asymmetric and site-selective formal [3 + 2]-annulations of γ-alkyl-β,γ-unsaturated γ-lactams with α,β-unsaturated aldehydes have been developed. These organocatalysed transformations yield high value enantioenriched bicyclic γ-lactams with up to four new stereocenters (sometimes including a quarternary carbon). The overall transformation starts from simple and readily accessible furans and oversees a rapid, controlled, and dramatic enhancement in 3D complexity.
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spelling pubmed-58222182018-02-26 Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams Kalaitzakis, Dimitris Sofiadis, Manolis Triantafyllakis, Myron Daskalakis, Konstantinos Vassilikogiannakis, Georgios Org Lett [Image: see text] Asymmetric and site-selective formal [3 + 2]-annulations of γ-alkyl-β,γ-unsaturated γ-lactams with α,β-unsaturated aldehydes have been developed. These organocatalysed transformations yield high value enantioenriched bicyclic γ-lactams with up to four new stereocenters (sometimes including a quarternary carbon). The overall transformation starts from simple and readily accessible furans and oversees a rapid, controlled, and dramatic enhancement in 3D complexity. American Chemical Society 2018-02-08 2018-02-16 /pmc/articles/PMC5822218/ /pubmed/29417818 http://dx.doi.org/10.1021/acs.orglett.8b00076 Text en Copyright © 2018 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kalaitzakis, Dimitris
Sofiadis, Manolis
Triantafyllakis, Myron
Daskalakis, Konstantinos
Vassilikogiannakis, Georgios
Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title_full Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title_fullStr Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title_full_unstemmed Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title_short Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
title_sort asymmetric and site-selective [3 + 2]-annulations for the synthesis of high-value bicyclic lactams
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5822218/
https://www.ncbi.nlm.nih.gov/pubmed/29417818
http://dx.doi.org/10.1021/acs.orglett.8b00076
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