Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by Aza-Belluš–Claisen Rearrangement,Organic Letters

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Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by Aza-Belluš–Claisen Rearrangement
Organic Letters ( IF 4.9 ) Pub Date : 2021-10-15 , DOI: 10.1021/acs.orglett.1c03187
Jiangqun Cheng ₁ , Yuan-He Li ₂ , Jun Huang ₁ , Zhen Yang _{1,

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Affiliation

Diastereoselective syntheses of syn- and anti-vicinal dihalides were achieved via an aza-Belluš–Claisen rearrangement, which involved the reaction of an α-chloro carboxylic acid chloride with halogen-substituted trans-allyl morpholines in the presence of Lewis acids. The developed method was used for the total synthesis of a group of monoterpene natural products bearing vicinal dichloride subunits.

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