Synfacts 2010(11): 1255-1255  
DOI: 10.1055/s-0030-1258743
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Asymmetric Cross-Coupling of Allyl Carbonates and Allyl Boronates

Contributor(s): Hisashi Yamamoto, Patrick Brady
P. Zhang, L. A. Brozek, J. P. Morken*
Boston College, Chestnut Hill, USA
Further Information

Publication History

Publication Date:
21 October 2010 (online)

Significance

The authors describe here a high-yielding, highly regio- and enantioselective cross-coupling of allyl carbonates and allyl boro­nates. Remarkably, nearly identical results are obtained for regioisomers 1 and 2. Importantly, aromatic and aliphatic allyl carbonates are tolerated under the reaction conditions. Allyl-allyl coupling in high regio- and stereoselectivity is a long-standing challenge in organic synthesis and this method provides an excellent solution.