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Synfacts 2005(3): 0310-0310  
DOI: 10.1055/s-2005-916136
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Allylic Transfer Reaction of Diene with Diboronyl Reagent and Aldehydes

Contributor(s): Mark Lautens, Josephine Yuen
C.-M. Yu*, J. Youn, S.-K. Yoon, Y.-T. Hong
Sungkyunkwan University, Korea
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

A highly regio- and stereoselective sequential allylic transfer of a diene with two aldehydes has been developed. The reaction is catalyzed by nickel and a diboronyl reagent to furnish four contiguous stereocenters in one step. The reaction has been successfully applied to six-membered rings with up to 10:1 diastereomeric ratio. Both diastereomers are accessible in high diastereoselectivity depending on the temperature:
-78 °C leading to B and 20 °C leading to A.