Xiang Ji, Shengwen Yang, Zhifei Zhao and Shi-Wu Li
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Catalytic asymmetric synthesis of guaiazulene analogues†
The asymmetric Michael addition reaction of guaiazulene to α,β-unsaturated 2-acyl imidazoles was developed with a chiral-at-metal Rh(III) complex as the catalyst for the first time. The corresponding adducts were obtained in good yields (76–98%) with excellent enantioselectivities (up to 99%). The reaction could be conducted on a gram-scale with a low catalyst loading (0.05 mol%) without impacting its efficiency. DFT studies rationalize the enantioselectivity of the reaction.