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term. See Hudlick’s discussion on this topic.¹b The
term tandem reaction is often used in
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the term domino reaction is preferred.²a Multicomponent reactions are a subclass
of domino reactions in which three or more components combine to form
a single product that essentially incorporates all the reactants
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reactions are domino processes; subsequent addition of reagents
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14 For a more detailed discussion of
the reaction pathway, see refs. 13a and 13b.
15 The use of an alkali metal hydroxide
(KOH) as the base caused an increase in the side product 6; see ref. 13a.
16 The formation of nitrone 6 as the major product is in accordance
with our previous observations of the reactivity of the allenyl
oxime 1; see ref. 13a.
17 The relative conversion was determined
by using diphenyl ether as an internal standard. A value corresponding
to 100% conversion was obtained by analysis of the reaction performed
at 80 ˚C for 3 h.
18 Zinc(II) bromide and copper(II) bromide
were also tested as Lewis acid catalysts and 1,4-diazabicyclo[2.2.2]octane (DABCO)
was tested as a Lewis base catalyst; the same results were obtained
in each case.
19 For more-detailed information about
the purity of the reaction product, see the supplementary material
for this article.
20 Enolizable aldehydes were also found
to be unsuitable as reaction components.
21 We also attempted the synthesis of
nitrones functionalized at position 4 of the nitrone skeleton by
employing substituted derivatives of allenyl oxime 1;
however, none of these reactions was successful.
22 Carbon (gray), oxygen (red), and
nitrogen (blue) atoms are drawn as principal ellipses (70% probability
level). Hydrogen atoms are drawn as fixed-size spheres (cyan).
23 Crystallographic data for compounds 4a and 4l have
been deposited with the accession numbers CCDC 822444 and 822443,
respectively, and can be obtained free of charge from the Cambridge
Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ,
UK; Fax: +44(1223)336033;
E-mail: deposit@ccdc.cam.ac.uk;
Web site: www.ccdc.cam.ac.uk/conts/retrieving.html.
24
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