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Synlett 1990; 1990(2): 111-113
DOI: 10.1055/s-1990-34712
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Synthesis of Aminoerythrose and of Aminoerythritol Derivatives via Diels-Alder Cycloadditions of 1-tert-Butyldimethylsiloxybutadiene with Acylnitrose Dienophiles

Albert Defoin* , Joaquim Pires, Jacques Streith
  • *Ecole Nationale Supérieure de Chimie, Université de Haute-Alsace, 3 rue Alfred Werner, F-68093 Mulhouse Cedex, France
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Publication Date:
08 March 2002 (online)

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1-tert-Butyldimethylsiloxybutadiene (1) reacted smoothly with acylnitroso dienophiles 2 to give the expected primary Diels-Alder cycloadducts 3 and 4. Sequential cis-hydroxylation and hydrogenolysis of these adducts led to the pyrrolidino-erythrose derivative 7 and to the polyhydroxylated amines 8, 11 and 14, depending on the nature of the reducing agent.