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Synfacts 2009(11): 1232-1232  
DOI: 10.1055/s-0029-1218126
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Heck Reaction of Allylic Esters with Arenediazonium Salts

Contributor(s): Mark Lautens, Chit Tsui
A. Venturini Moro, F. Sega Pareira Cardoso, C. Roque Duarte Correia*
Universidade Estadual de Campinas, São Paulo, Brazil
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Publication History

Publication Date:
22 October 2009 (online)

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Significance

The Heck arylation of olefins is a powerful method for the efficient formation of Csp2 -Csp2 bonds. The use of allylic esters in Heck reactions poses challenges since these are common substrates for the well-known Tsuji-Trost reaction. The authors report herein a mild, efficient and highly stereo- and regioselective Heck arylation of allylic esters employing arenediazonium salts. This new Heck protocol can be extended to a vinylic lactone towards the efficient and concise synthesis of yangonine, a bioactive kavalactone.