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β-Siloxy-α-haloketones through Highly Diastereoselective Single and Double Mukaiyama Aldol Reactions

Authors

  • Dr. Jakub Saadi,

    1. Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60635 (USA), Fax: (+1) 773-702-5059
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  • Prof. Dr. Hisashi Yamamoto

    Corresponding author
    1. Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60635 (USA), Fax: (+1) 773-702-5059
    • Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60635 (USA), Fax: (+1) 773-702-5059
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Abstract

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Double-action haloketones: A super silyl group enabled the first highly diastereoselective Mukaiyama aldol reactions of α-chloro- and α-fluoroketones with a wide range of aldehydes, providing anti-β-siloxy-α-haloketones. This process is compatible with one-pot double-aldol methodology and allows for rapid access to new halogen-modified polyketide fragments bearing up to four contiguous stereocenters (see scheme).

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