Organic Letters
Organic Letters
5 years ago

Enantioselective Michael Addition of Photogenerated o-Quinodimethanes to Enones Catalyzed by Chiral Amino Acid Esters

Enantioselective Michael Addition of Photogenerated o-Quinodimethanes to Enones Catalyzed by Chiral Amino Acid Esters
Shupeng Dong, Guibing Wu, Chuncheng Zou, Xiaoqian Yuan, Zhen Liu, Jinxing Ye
The first example of a photoexcitated amine-catalyzed process for asymmetric Michael addition of o-quinodimethanes to enones is described. In the presence of simple chiral amino acid esters, a variety of Michael adducts were generally obtained in good yields and excellent stereoselectivities. This strategy can be successfully applied to 3-substituted-2-cyclohexenones and provides an asymmetric access to all-carbon quaternary centers. Furthermore, the high stereocontrol was explained by means of density-functional theory (DFT) calculations.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00862

DOI: 10.1021/acs.orglett.7b00862

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