Chiral cyclohexanones are a common structural motif of many natural products, biologically active molecules and are used as a building blocks in organic synthesis.1 Because of their useful applications, several methodologies have been developed in the literature for the asymmetric synthesis of cyclohexanones frameworks.2 However, there is no catalytic method reported so far in the literature for the asymmetric synthesis of disubstituted 4-oxocyclohexanecarbaldehydes. Acetone is one of the common organic solvents used in organic chemistry. Use of acetone as a substrate for chemical reactions is always a challenging and attractive task for organic chemists because of its inert nature, inexpensive, and easy availability. Herein, we have described the first organocatalytic stereoselective domino reaction from the readily available acetone and cinnamaldehyde derivatives to disubstituted 4-oxocyclohexanecarbaldehydes in up to 71% yield, up to 13:1 diastereoselectivity, and up to >99% enantioselectivity using two secondary amine catalysts.3
References
1. (a) Liao, H. X.; Zheng, C. J.; Huang, G. L.; Mei, R. Q.; Nong, X. H.; Shao, T. M.; Chen, G. Y.; Wang, C. Y. J. Nat. Prod. 2019, 82, 2211–2219. (b) Wang, J.; Duan, H.; Wang, Y.; Pan, B.; Gao, C.; Gai, C.; Wu, Q.; Fu, H. J. Nat. Prod. 2017, 80, 19–29.
2. (a) Halland, N.; Aburel, P. S.; Jørgensen, K. A. Angew. Chem. Int. Ed. 2004, 43, 1272–1277. (b) Liang, J.; Chen, Q.; Liu, L.; Jiang, X.; Wang, R. Org. Biomol. Chem. 2013, 11, 1441–1445. (c) Yang, H.; Wang, Q.; Luo, Y.; Ye, L.; Li, X.; Chen, F.; Zhao, Z.; Li, X. Org. Biomol. Chem. 2020, 18, 1607–1611.
3. Maurya, V.; Kutwal, M. S.; Appayee, C. Org. Lett. 2021, 23, 1566–1571.

Direct Catalytic Asymmetric Synthesis of Disubstituted 4-Oxocyclohexanecarbaldehydes from Acetone and Cinnamaldehyde Derivatives

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