Issue 19, 2013

Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Jan 2013
Accepted
06 Mar 2013
First published
07 Mar 2013

Org. Biomol. Chem., 2013,11, 3128-3144

Asymmetric synthesis of carbocycles: use of intramolecular conjugate displacement

D. T. Sreedharan and D. L. J. Clive, Org. Biomol. Chem., 2013, 11, 3128 DOI: 10.1039/C3OB40115D

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