Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 65, No. 4, 2005, pp.823-841
Published online, 22nd February, 2005
DOI: 10.3987/COM-05-10335
Yb(OTf)3-catalyzed Vinylogous Mannich Reaction of Trialkylsilyloxyfuran

Sylvain Oudeyer, Bruno Dudot, and Jacques Royer*

*CNRS-University Paris5, Faculty of Pharmacy, 4 avenue de l’Observatoire, 75270 Paris Cedex 06, France


The one-pot three-component vinylogous Mannich reaction of trialkylsilyloxyfurans with anilines and aldehydes in the presence of catalytic amounts of Yb(OTf)3 gave the substituted aminoalkyl-butenolides in good yields (> 90 %) and diastereoselectivities (d.e. > 60 %). The configuration of the major product is erythro (anti) and was confirmed by chemical transformation into piperidinone derivatives and 1H NMR spectral studies of the latter compounds. The vinylogous Mannich reaction performed with preformed imines proceeded similarly with a preferred erythro selectivity while the condensation of 3-methyl-2-trialkylsilyloxyfurans was threo selective.