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Synfacts 2011(4): 0416-0416  
DOI: 10.1055/s-0030-1259643
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 1,3-Diols through Grignard Addition to Isopropenyl Acetate

Contributor(s): Mark Lautens, Stephen G. Newman
Y. Jiao, C. Cao*, Z. Zhou
Central South University, Changsha and Hunan University of Science and Technology, Xiangtan, P. R. of China
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Publikationsdatum:
18. März 2011 (online)

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Significance

The 1,3-diol moiety is frequently found in many important natural products and pharmaceuticals. Many methods have been ­developed to synthesize 1,3-diols with both syn- and anti-relative stereochemistry. The authors present a unique and unexpected reaction to form anti-1,3-diols from isopropenyl acetate and aryl Grignard reagents in moderate yield and good ­selectivity for the anti diastereomer.