Diels-Alder reactions tandem, with sigmatropic

Tandem reactions combining Diels-Alder reactions with sigmatropic rearrangements in syntheses of heterocycles 98S227. 

Neuschuetz K., Velker J., Neier R. Tandem Reactions Combining Diels-Alder Reactions With Sigmatropic Rearrangement Processes and Their Use in Synthesis Synthesis 1998 227-255... 

Neuschiitz, K. Velker, J. Neier, R. (1998) Tandem reactions combining Diels-Alder reactions with sigmatropic rearrangement processes and their use in synthesis. Synthesis, 3, 227-55. 

Combination of a Diels-Alder reaction and a [3,3] sigmatropic rearrangement provides access to 1,4-substituted 2-cyclohexenyl derivatives75- 76,11 . Thus, Diels-Alder reaction of ( )-l,3-bu-tadienyl thiocyanate with methyl acrylate is followed by a [3,3] sigmatropic rearrangement to the isothiocyanate. The isothiocyanate is trapped by the solvent to give racemic 0-cthyl-/V-(4-methoxycarbonyl-2-cyclohexcnyl)thiocarbamate in a 66 33 diastereomeric ratio (cisjtram). A Lewis acid catalyzed variant of this tandem reaction showed better diastereoselectivity (90 10)111. 

Victoria Gomez M, Aranda Al et al (2009) Microwave-assisted reactions of nitrohetero-cycles with dienes. Diels-Alder and tandem hetero Diels-Alder/[3, 3] sigmatropic shift. Tetrahedron 65 5328-5336... 

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