Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement

作者：Sreedharan Dinesh T; Clive Derrick L J^*

来源：Organic and Biomolecular Chemistry, 2013, 11(19): 3128-3144.

DOI：10.1039/c3ob40115d

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 gamma- or delta-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.

• 出版日期2013