56239-25-9Relevant articles and documents
α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights
Calvet, Géraldine,Coote, Susannah C.,Blanchard, Nicolas,Kouklovsky, Cyrille
supporting information; scheme or table, p. 2969 - 2980 (2010/06/20)
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.
Polyhydroxyamino Compounds via Diene Synthesis with Nitroso Compounds, IV. - Preparation and Stereochemistry of Dideoxyinosamine Derivatives
Kresze, Guenter,Kysela, Ernst
, p. 202 - 209 (2007/10/02)
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.