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Synfacts 2009(11): 1247-1247
DOI: 10.1055/s-0029-1218129
DOI: 10.1055/s-0029-1218129
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Auxiliary-Based Diastereoselective Roskamp Reaction
T. Hashimoto, H. Miyamoto, Y. Naganawa, K. Maruoka*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
22 October 2009 (online)
Significance
The authors report on an auxiliary-based diastereoselective version of the Roskamp reaction (C. R. Holmquist, E. J. Roskamp J. Org. Chem. 1989, 54, 3258). Development of a selective variant has been hindered by product epimerization and competing reaction pathways. Camphorsultam auxiliary appears to solve both the chemoselectivity and stability obstacle, giving products isolable in high yields and diastereomeric ratios.