Synthetic Studies on the MARDi Cascade: Stereoselective Preparation of Sulfonyl-Substituted Seven-Membered Rings

Abstract

A stereoselective synthesis of functionalized sulfonyl-substituted cycloheptanes is described. The approach involves a ­formal two-carbon ring expansion of 2-benzenesulfonyl cyclopentanones through a base-induced anionic domino three-component transformation named the MARDi cascade.

stereoselective synthesis - domino reactions - multi-component reactions - ring expansion - cycloheptane

References and Notes

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The structure of the cycloheptenic acids 3 has been reviewed and confirmed to be as depicted in Scheme [1] by X-ray diffraction analysis of the derivative A (Scheme [3] ; see ref. 9). The full detailed study of the MARDi cascade will be reported in due time.

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For examples of sulfonyl-substituted cycloheptanes, see:

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<A NAME="RG21006ST-9">9</A>

Crystallographic data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, with CCDC numbers 615710, 615708, 615709 for com­-pounds A, 8 and 9, respectively. Copies of this information can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: [phone]; E-mail: [e-mail] or www: http://www.ccdc.cam.ac.uk].