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Novel IBX‐Mediated Processes for the Synthesis of Amino Sugars and Libraries Thereof
Author(s) -
Nicolaou K. C.,
Baran Phil. S.,
Zhong YongLi,
Vega Juan A.
Publication year - 2000
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 - 10.1002/1521-3773(20000717)39:14<2525::aid-anie2525>3.0.co;2-1
Subject(s) - sugar , combinatorial chemistry , chemistry , mechanism (biology) , amino acid , scheme (mathematics) , production (economics) , organic chemistry , biochemical engineering , computer science , biochemistry , engineering , mathematics , economics , philosophy , epistemology , mathematical analysis , macroeconomics
The cyclization of N ‐arylcarbamates onto olefins , orchestrated by IBX, is a new synthetic method for the preparation of diverse arrays of amino sugar building blocks (see scheme for an example). A revised proposal for the mechanism of this novel reaction is also disclosed, which leads to the discovery of a remarkable interaction of IBX and glycals. The new reactions have potential in the production of libraries for biological screening. IBX= o ‐iodoxybenzoic acid = 1‐hydroxy‐1,2‐benziodoxol‐3(1 H )‐one 1‐oxide.