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Synfacts 2010(11): 1265-1265
DOI: 10.1055/s-0030-1258592
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
T. Hashimoto, Y. Naganawa, K. Maruoka*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
21 October 2010 (online)
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.