Abstract
Hetero Diels-Alder reaction in which the C-nitroso moiety (R-N=0) functions as a heterodienophile provides cyclic derivatives of hydroxylamine namely 3,6-dihydro-l,2-oxazines 1 (ref. 1). A synthetically important feature of the products is introduction of nitrogen and oxygen functionality at the same time with a high degree of regiochemical and stereochemical control. Subsequent reduction of these cycloadducts can easily be achieved by using a wide variety of reducing agents, such as zinc in acetic acid, sodium or aluminum amalgam in ethanol, or hydrogen over catalysts, and normally result in cleavage of the N-O bond leading to the formation of 4-amino alcohols.
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