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One-pot cross-coupling of N-acyl N,O-acetals with alpha,beta-unsaturated compounds.

Chemical communications (Cambridge, England) (2009-11-12)
Yong-Gang Xiang, Xiang-Wu Wang, Xiao Zheng, Yuan-Ping Ruan, Pei-Qiang Huang
RÉSUMÉ

The synergistic action of BF(3).OEt(2) and SmI(2) allowed a series of intermolecular cross-couplings of readily available N-acyl N,O-acetals with alpha,beta-unsaturated compounds to be performed in high yields, which was applied to the stereoselective synthesis of pyrrolizidine alkaloid (+)-xenovenine.

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Sigma-Aldrich
Boron trifluoride diethyl etherate, for synthesis
Sigma-Aldrich
Boron trifluoride diethyl etherate, purified by redistillation, ≥46.5% BF3 basis