Dearomatization reactions, which can convert widespread aromatic systems into functionalized compounds in high efficiency, are quite useful in the total synthesis of natural products. On the other hand, the electrophilic α-amination of carbonyl compounds is an efficient synthetic method to construct α-amino carbonyl motifs. The dearomatization of 2-naphthols through an amination reaction with azodicarboxylates can construct a unique β-naphthalenone skeleton with a chiral quaternary carbon centre, which are important components of various biologically active natural products and therapeutic reagents. A catalytic asymmetric dearomatization of 2-naphthols with azodicarboxylates has been accomplished by using a N,N'–dioxide-scandium(III) complex as chiral catalyst. A number of optically active β-naphthalenone compounds with a nitrogen-containing quaternary carbon stereocenter were obtained in up to 99% yield and up to 99% ee under mild reaction conditions. Based on these experiments and on previous reports, a possible transition state was proposed. Reference [1] X. H. Liu, L. L. Lin, X. M. Feng, Acc. Chem. Res. 2011, 44 , 574-587; [2] X. H. Liu, L. L. Lin, X. M. Feng, Org. Chem. Front. 2014, 1, 298-302; [3] X. J. Lian, S. S. Guo, G. Wang, L. L. Lin, X. H. Liu, X. M. Feng, J. Org. Chem. 2014, 79, 7703-7710; [4] X. J. Lian, L. L. Lin, G. J. Wang, X. H. Liu, X. M. Feng, Chem. Eur. J. 2015， DOI : 10.1002/chem.201503276.

Chiral N,N'–dioxide-scandium(III)-catalyzed asymmetric dearomatization of 2-naphthols through an amination reaction

251st National Meeting (2016)

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