[reaction: see text] A new, robust tert-butyldiarylsilyl (TBDAS) linker has been developed for solid-phase organic synthesis. This linker is stable to both protic and Lewis acidic reaction conditions, overcoming a significant limitation of previously reported silyl linkers. Solid-phase acetal deprotection, olefination, asymmetric allylation, and silyl protecting group deblocking reactions have been demonstrated with TBDAS-linked substrates.
[Show abstract][Hide abstract] ABSTRACT: 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.
[Show abstract][Hide abstract] ABSTRACT: Organic transformations on substrates which are immobilized on an insoluble, polymeric carrier have found broad application in compound collection synthesis. In contrast to other synthetic methodologies in solid-phase organic synthesis, reactions that afford non-racemic products are strikingly under-represented. Not only does the introduction of stereoinformation on immobilized, achiral starting materials provide enantioenriched products which can be of value for biological testing, but it also opens up new perspectives for accessible structures. This feature article gives an overview of successful enantioselective transformations on a solid support. Critical differences in the corresponding solution-phase protocols are highlighted, and applications to the generation of compound collections are particularly mentioned.
Chemical Communications 09/2006; 37(32):3380-9. DOI:10.1039/b602822e · 6.83 Impact Factor
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