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Synfacts 2006(11): 1159-1159
DOI: 10.1055/s-2006-949488
DOI: 10.1055/s-2006-949488
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Cu-Catalyzed Catalytic Diboration of Aldehydes
D. S. Laitar, E. Y. Tsui, J. P. Sadighi*
Massachusetts Institute of Technology, Cambridge, USA
Further Information
Publication History
Publication Date:
24 October 2006 (online)

Significance
Methods of formation of a new carbon-heteroatom σ-bond are highly desirable for synthetic organic chemistry. The authors developed the first practical method for the direct addition of boranes to the C=O bond, leading to α-hydroxyboranes, potentially useful equivalents of α-oxycarbanions. The reaction proceeds smoothly with a variety of aryl-, hetaryl-, and alkylcarbaldehydes, affording uniformly high yields of products. The resulting boronic esters are sufficiently stable for isolation and storage and open an interesting perspective for use in synthesis.