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A Structurally Diverse Library of Polycyclic Lactams Resulting from Systematic Placement of Proximal Functional Groups
Author(s) -
Mitchell Judith M.,
Shaw Jared T.
Publication year - 2006
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/anie.200503341
Subject(s) - enantioselective synthesis , oxazole , sequence (biology) , cycloaddition , aldehyde , computer science , stereochemistry , combinatorial chemistry , chemistry , catalysis , organic chemistry , biochemistry
A short, linear sequence for the synthesis of complex small polycyclic lactams (see picture) is presented. The sequence, which is applied to the synthesis of a library of 529 compounds, is based on a catalytic, enantioselective cycloaddition between an oxazole and an aldehyde, so that the resultant compounds are enantiomerically pure and readily prepared in either stereochemical series.