α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights
α-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a β-oxygenated moiety led to a domino [4+2] cycloaddition/σN-O bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the σN-O bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported.
Intermolecular nitroso Diels-Alder cycloaddition of α-acetoxynitroso derivatives in aqueous medium
The Diels-Alder cycloadditions of the α-acetoxynitroso dienophile 1 in water are reported. The rapid and high yielding synthesis of structurally diverse 3,6-dihydro-1,2-oxazines complements the straightforward elaboration of aminoalcohols obtained from th
Polyhydroxyamino Compounds via Diene Synthesis with Nitroso Compounds, IV. - Preparation and Stereochemistry of Dideoxyinosamine Derivatives
The general method for the synthesis of polyhydroxy amines by Diels-Alder reactions with a nitroso compound, reduction of the adduct with cleavage of the N - O bond and hydroxylation of the remaining C = C -double bond, can also be realized with α-chloronitrosocyclohexane as dienophile, in good yield.Primary amines are synthesized in this way.
Kresze, Guenter,Kysela, Ernst
p. 202 - 209
(2007/10/02)
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