Conjugate addition/Ireland-Claisen rearrangements of allyl fumarates: simple access to terminally differentiated succinates.

Autor: Bausch CC; Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290, USA., Johnson JS
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2008 Feb 15; Vol. 73 (4), pp. 1575-7. Date of Electronic Publication: 2008 Jan 23.
DOI: 10.1021/jo701778k
Abstrakt: The conjugate addition of dialkylzinc reagents to allyl fumarates with subsequent Ireland-Claisen rearrangement has been accomplished yielding substituted unsymmetrical succinic acid derivatives. This one-pot reaction creates two new carbon-carbon bonds at contiguous stereogenic centers. The reaction proceeds for several alkylzinc reagents and substituted allyl fumarates. The products contain distinguishable functional handles for further manipulation.
Databáze: MEDLINE