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. 2014 Dec 5;16(23):6260-3.
doi: 10.1021/ol503248f. Epub 2014 Nov 20.

Palladium-catalyzed Stereoretentive Olefination of Unactivated C(sp3)-H Bonds With Vinyl Iodides at Room Temperature: Synthesis of β-Vinyl α-Amino Acids

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Palladium-catalyzed Stereoretentive Olefination of Unactivated C(sp3)-H Bonds With Vinyl Iodides at Room Temperature: Synthesis of β-Vinyl α-Amino Acids

Bo Wang et al. Org Lett. .

Abstract

A method is reported for palladium-catalyzed N-quinolyl carboxamide-directed olefination of the unactivated C(sp(3))-H bonds of phthaloyl alanine with a broad range of vinyl iodides at room temperature. This reaction represents the first example of the stereoretentive installation of multisubstituted terminal and internal olefins onto unactivated C(sp(3))-H bonds. These methods enable access to a wide range of challenging β-vinyl α-amino acid products in a streamlined and controllable fashion, beginning from simple precursors.

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