Ansa Macrolides as Molecular Workbenches: Stereocontrolled syn Additions to E olefins

Ansa Macrolides as Molecular Workbenches: Stereocontrolled syn Additions to E olefins

Fixed on an aromatic platform in a conformationally defined way, acyclic (E)‐alkenes can be considered gripped on a molecular workbench. The olefinic ansa‐macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place di...

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Veröffentlicht in:Angewandte Chemie International Edition 1998-06, Vol.37 (11), p.1566-1569
Hauptverfasser: Mulzer, Johann, Schein, Karin, Bats, Jan W., Buschmann, Jürgen, Luger, Peter
Format: Artikel
Sprache:eng
Schlagworte:
Diastereoselective reactions
Dihydroxylations
Epoxidations
Macrocycles
Protecting groups
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Beschreibung
Zusammenfassung:Fixed on an aromatic platform in a conformationally defined way, acyclic (E)‐alkenes can be considered gripped on a molecular workbench. The olefinic ansa‐macrolides formed in this way are shielded on one face. On epoxidation and dihydroxylation [Eq. (1)] the attack on the double bond takes place diastereoselectively from outside the ring, and the ansa chain can subsequently be cleaved from the workbench by mild hydrogenolysis. Bn=benzyl, NMO=N‐methylmorpholin‐N‐oxide.
ISSN:1433-7851
1521-3773
DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U