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Synfacts 2009(7): 0772-0772
DOI: 10.1055/s-0029-1217272
DOI: 10.1055/s-0029-1217272
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Diastereoselective Synthesis of Chiral Tertiary Methyl Ethers
B. Checa, E. Gálvez, R. Parelló, M. Sau, P. Romea*, F. Urpí*, M. Font-Bardia, X. Solans
Universitat de Barcelona, Spain
Further Information
Publication History
Publication Date:
22 June 2009 (online)
Significance
An auxiliary-based synthesis of chiral tertiary methyl ethers 3 through addition of titanium enolates to dialkyl ketals is reported. The products, obtained in good yields and moderate selectivities, are densely functionalized and constitute an important class of chiral synthons. The motif is difficult to obtain through aldol condensation owing to the low reactivity of ketones; however, examples can be found utilizing chiral auxiliaries (P. C. Bulman Page and co-workers J. Org. Chem. 2000, 65, 6027) or chiral catalysts (M. Shibasaki and co-workers J. Am. Chem. Soc. 2006, 128, 7164). Reductive aldol reactions have also been applied (O. Riant and co-workers Angew. Chem. Int. Ed. 2006, 45, 1292).