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Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement†
Dinesh T. Sreedharan,Derrick L. J. Clive
Organic & Biomolecular Chemistry Pub Date : 03/07/2013 00:00:00 , DOI:10.1039/C3OB40115D
Abstract

Intramolecular conjugate displacement (ICD), the process illustrated in eqn (1), has been applied to the Morita–Baylis–Hillman adducts formed from (5S)-5-(L-menthyloxy)-2(5H)-furanone and aldehydes that are substituted in the γ- or δ-position by geminal phenylthio groups. When the initial Morita–Baylis–Hillman alcohols are acetylated and oxidized to geminal sulfones, deprotonation causes ring closure by ICD (2.5→2.6). Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle.

Graphical abstract: Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement
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