Organocatalysis aldehyde domino reaction

Chiral secondary amines are another important class of privileged functional component in dual organocatalysis that has been widely used in asymmetric catalysis [39]. For example, in 2008, Cordova et al. [40] reported the combinational use of (S)-diphenylprolinol TMS ether (127) and Br0nsted base DABCO (128) as dual organocatalysts to promote the asymmetric domino double Michael addition reaction (nitro-Michael/Michael reaction) of 5-nitropentenoate (125) to a,(i-unsaturated aldehydes (Scheme 43.26), which gave the corresponding nitrogen-,... 

Later, the cascade three-component organocatalysis was applied in the first enantioselective total synthesis of (-l-)-coni-col (Scheme 21.34). The synthesis was achieved via a key step reaction involving the organocatalytic domino oxa-Michael-Michael-Michael-aldol condensation of 2-( )-2-nitro-vinyl)benzene-l,4-diol 148, 3-methylbut-2-enal 145, and ( )-4,4-dimethoxybut-2-enal 150. The successful synthesis further expands the realm of the reactant of this three-component reaction beyond 3-arylacrylaldehyde to the a, 3-unsaturated aldehydes bearing a y-H. 

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