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Org Biomol Chem
; 11(19): 3128-44, 2013 May 21.
Article
in English
| MEDLINE
| ID: mdl-23536216
ABSTRACT
Intramolecular conjugate displacement (ICD), the process illustrated in , 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 (2.5â2.6). Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle.