Annulative Morita–Baylis–Hillman reaction to synthesise chiral dibenzocycloheptanes. Issue 73 (23rd August 2021)

• Record Type: Journal Article
• Authors: Mondal, Atanu; Shivangi, ; Tung, Pinku; Wagulde, Siddhant V.; Ramasastry, S. S. V.
• Is Part Of: Chemical communications. Volume 57:Issue 73(2021)
• Page Start: 9260
• Page End: 9263
• Publication Date: 2021-08-23
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d1cc02765d
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The synthesis of racemic and chiral dibenzocycloheptanes has been achieved by employing the intramolecular Morita–Baylis–Hillman reaction as the key step. Abstract : We describe the first metal-free and organocatalytic strategy to access highly functionalised dibenzocycloheptanes via a phosphine-promoted annulative Morita–Baylis–Hillman (MBH) reaction. The method is manipulated to access to chiral dibenzocycloheptanes as well. This work represents a rare entry for the construction of seven-membered carbocycles via the MBH route. The realisation of several bioactive molecules possessing the dibenzocycloheptane core makes this an attractive strategy.