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Nitroso-dienophile additions to dendralenes: A short synthesis of branched aminosugars

Wang, Ruomeng (Cynthia); Bojase-Moleta, Gomotsang; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael


The first heteroatom-based dienophile cycloadditions to cross-conjugated alkenes ([n]dendralenes) are reported. Nitroso-dienophiles undergo smooth single and double Diels-Alder additions to the parent dendralenes with orientational regio- and stereoselectivity and, notably, with reactivity that depends upon the parity of the [n]dendralene. The first crystal structure of a cross-conjugated hexaene is reported. Vasellas nitroso-sugar reagent gives a highly enantiomerically enriched double...[Show more]

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
Source: Organic Letters
DOI: 10.1021/ol302619r


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