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Synfacts 2010(8): 0901-0901  
DOI: 10.1055/s-0030-1257776
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Nickel-Catalyzed Reductive Coupling of Dienes with Aldehydes

Contributor(s): Mark Lautens, Stephen G. Newman
H. Y. Cho, J. P. Morken*
Boston College, Chestnut Hill, USA
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Reactions forming multiple stereocenters from simple starting materials are highly desirable to improve synthetic efficiency. The authors present a highly diastereoselective borylative coupling of 1,3-pentadiene with aldehydes. The products contain three contiguous stereocenters and a highly desirable syn-1,3-diol motif, commonly found in polyketides and other natural products.