1432519-22-6Relevant articles and documents
Asymmetric synthesis of carbocycles: Use of intramolecular conjugate displacement
Sreedharan, Dinesh T.,Clive, Derrick L. J.
, p. 3128 - 3144 (2013/06/04)
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. The Royal Society of Chemistry 2013.