Publication:
Enantioselective Formation of 2-Azetidinones by Ring-Assisted Cyclization of Interlocked N-(alpha-Methyl)benzyl Fumaramides

Thumbnail Image
Files
2020ACIE_AV_Enantioselective Ring-Assisted Cyclization of Interlocked Fumaramides.pdf(846.49 KB)
Date
2018-04-16
relationships.isAuthorOfPublication
relationships.isSecondaryAuthorOf
relationships.isDirectorOf
Authors
Martinez-Cuezva, Alberto ; Bautista, Delia ; Alajarín, Mateo ; Berná Cánovas, José
item.page.secondaryauthor
item.page.director
Publisher
WILEY-VCH VERLAG GMBH
publication.page.editor
publication.page.department
Química Orgánica
DOI
10.1002/anie.201803187
item.page.type
info:eu-repo/semantics/article
Description
Abstract
The synthesis of optically active interlocked and non-interlocked 2-azetidinones by intramolecular cyclization of N-(alpha-methyl)benzyl fumaramide [2]rotaxanes is described. Two different strategies of asymmetric induction were tested in which the chiral group was located either proximal or distal to the reacting center of the thread. During these experiments, an interesting equilibration process inside the macrocyclic void occurred, thus leading to the cyclization through the (alpha-methyl)benzyl carbon atom and giving rise to beta-lactams, with a quaternary carbon atom, in an enantio- and diastereocontrolled manner. This cyclization also proceeds in kinetically stable chiral pseudo[2]rotaxanes, thus allowing further de threading to provide enantioenriched 3,4-disubstituted trans-2-azetidinones. The stereochemical outcomes of the cyclization inside and outside the macrocycle demonstrated noticeable
publication.page.subject
Lactams , Rotaxanes , Stereoselectivity , Supramolecular chemistry , Template synthesis , Emerging applications
Citation
Angew. Chem. Int. Ed. 2018, 57, 6563.
URI
http://hdl.handle.net/10201/102606
item.page.embargo
Collections
Artículos
Ir a Estadísticas