24730-93-6Relevant articles and documents
Experimental studies on the selective β-c-h halogenation of enones
Huber, Tatjana,Kaiser, Daniel,Rickmeier, Jens,Magauer, Thomas
, p. 2281 - 2294 (2015/03/18)
Here we describe the realization of a one-pot protocol for the β-C-H halogenation of cyclic enones via umpolung of the β-carbon. The developed method includes hydrazone formation and selective β-halogenation (bromination, chlorination) with N-bromosuccini
[4+2] Cycloaddition of 1-dimethylamino-3-tert-butyldimethylsiloxy-1,3-butadiene with methyl acrylate: 4-hydroxymethyl-2-cyclohexen-1-one [ 2-cyclohexen-1-one, 4-(hydroxymethyl)- ]
Kozmin, Sergey A.,He, Shuwen,Rawal, Viresh H.,Figueroa, Ruth,Hart, David J.
, p. 160 - 160 (2017/09/23)
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Racemic and asymmetric Diels-Alder reactions of 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes
Janey,Iwama,Kozmin,Rawal
, p. 9059 - 9068 (2007/10/03)
Achiral and chiral 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes were prepared from readily available starting materials. Although more stable than the parent 1-amino-3-siloxy dienes, the 1-(2-oxazolidinon-3-yl)-3-siloxy-1,3-butadienes are still very reactive in Diels-Alder reactions, somewhat more than 1,3-dialkoxy-1,3-butadienes (e.g., Danishefsky's diene). The cycloadditions of the achiral and chiral dienes with several different dienophiles were examined. The reactions proceeded in good yield, with modest to high endo selectivity. The chiral dienes exhibited excellent facial selectivity in cycloadditions with α-substituted acroleins, maleic anhydride and N-phenylmaleimide. Upon reduction and hydrolysis of the cycloadducts, substituted cyclohexenones were obtained with ee's ranging from 22% to >98%.