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

Research paper by Ruomeng R Wang, Gomotsang G Bojase, Anthony C AC Willis, Michael N MN Paddon-Row, Michael S MS Sherburn

Indexed on: 31 Oct '12Published on: 31 Oct '12Published in: Organic Letters



Abstract

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. Vasella's nitroso-sugar reagent gives a highly enantiomerically enriched double cycloadduct with [3]dendralene. This bicyclic oxazine is successively dihydroxylated and then ring-opened to form a branched chain diamino tetrol.