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Synfacts 2010(11): 1265-1265  
DOI: 10.1055/s-0030-1258592
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrizing Asymmetric Ring Expansion of Cyclohexanones

Contributor(s): Mark Lautens, David A. Candito
T. Hashimoto, Y. Naganawa, K. Maruoka*
Kyoto University, Japan
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Publication History

Publication Date:
21 October 2010 (online)

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Significance

The authors report on the Lewis acid mediated reaction of chiral α-diazocarbonyl compound (+)-1 with cyclohexanones providing cyclic β-keto carbonyls bearing a kinetically stabilized α-hydrogen. This method reliably provides high selectivity and good yields for a range of different substrates. Furthermore, desymmetrization of meso-substrates allows for multiple stereocenters to be set in a single operation.