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Cinnamamides, 2+2 addition

Several types of unsaturated amides have produced gitonic superelectrophiles in superacidic media. For example, reaction of the cinnamamide (60) with benzene in CF3SO3H gives the addition product in quantitative yield (eq 20).27... [Pg.197]

Highly diastereoselective alkyl radical addition to Oppolzer s camphorsultam derivative (33) of oxime provides enantiomerically pure a-alkyl-a-amino acid derivative (34) at — 78 °C by the same method as shown in eq. 10.16. Moreover, enantioselective tandem radical 1,2-difunctionalization of cinnamamide (35) can be carried out with high stereoselectivity, using the chelation manner of the cinnamamide and a chiral bisoxazoline ligand on Mgl2, as shown in eq. 10.17. [Pg.225]

Ehrler and Farooq" prepared 1187 via a stepwise construction of the three thiazoline rings, introduction of the styryl group, and preparation of the oxazole ring (Scheme 1.333). Condensation of L-cysteine ethyl ester hydrochloride 1284 (R = C2H5) with an imino ether derived from cinnamamide was unsuccessful, owing to complications from Michael addition. This necessitated a strategy in which the styryl double bond was introduced after assembly of thiazoline rings. [Pg.288]

As mentioned above, 3-p- BocCiNH-a-CD forms helical supramolecular polymers in aqueous solutions. In contrast, 6-p- BocCiNH-) -CD was synthesized and found to form an intramolecular complex using NMR measurements. When adamanta-necarboxylic acid (1-AdCA) was added as a competitive guest to an aqueous solution of 6-p- BocCiNH- -CD, NMR spectra showed that the Boc-cinnamamide part in its own fi-CD cavity was expelled into water. The 6-p- BocCiNH- -CD underwent a conformational change to form an inclusion complex with AdCx. Moreover, with an addition of an excess amount of a-CD, the cinnamoyl part was found to be included in a-CD to form a hetero dimer (Fig. 3.27). [Pg.82]


See other pages where Cinnamamides, 2+2 addition is mentioned: [Pg.84]    [Pg.566]    [Pg.54]    [Pg.436]    [Pg.891]    [Pg.18]    [Pg.423]   
See also in sourсe #XX -- [ Pg.14 , Pg.18 ]




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Cinnamamide

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