Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement.
نویسندگان
چکیده
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 (2.5→2.6). Hydrogenation, DIBAL-H reduction and desulfonylation releases an optically pure carbocycle.
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ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 11 19 شماره
صفحات -
تاریخ انتشار 2013