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Ansa Macrolides as Molecular Workbenches: Stereocontrolled syn Additions to E olefins
Author(s) -
Mulzer Johann,
Schein Karin,
Bats Jan W.,
Buschmann Jürgen,
Luger Peter
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980619)37:11<1566::aid-anie1566>3.0.co;2-u
Subject(s) - workbench , hydrogenolysis , dihydroxylation , chemistry , double bond , ring (chemistry) , stereochemistry , organic chemistry , computer science , catalysis , enantioselective synthesis , artificial intelligence , visualization
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.