Download PDF
Synfacts 2007(8): 0841-0841  
DOI: 10.1055/s-2007-968723
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of 1,3-Enynes from Diiodoalkenes

Contributor(s): Mark Lautens, Frédéric Ménard
B. C. Ranu*, K. Chattopadhyay
Indian Association for the Cultivation of Science, Jadavpur, India
Further Information

Publication History

Publication Date:
24 July 2007 (online)

    Permissions and Reprints

Significance

A convergent Pd-catalyzed reaction was developed to prepare enynes in water. The nature of the electron-withdrawing group on the alkene dictated the stereochemical outcome of the enynoates 2 or 3 (for precedents, see: I. P. Beletskaya, A. V. Cheprakov Chem. Rev. 2000, 100, 3009). The reaction worked equally well with aromatic or alkyl substituents on the vicinal diiodoalkenes 1 or 4.