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Preparation of Chiral α-Substituted Alaninates through an Efficient Diastereoselective Synthesis of Trisubstituted Allylic Alcohols

Authors

  • Balraj Gopula,

    1. Department of Chemistry, National Taiwan Normal University, No. 88, Section. 4, Tingzhou Rd. Taipei, 11677, ROC (Taiwan), Fax: (+886) 2-29324249
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  • Prof. Dr. Way-Zen Lee,

    1. Department of Chemistry, National Taiwan Normal University, No. 88, Section. 4, Tingzhou Rd. Taipei, 11677, ROC (Taiwan), Fax: (+886) 2-29324249
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  • Prof. Dr. Hsyueh-Liang Wu

    Corresponding author
    1. Department of Chemistry, National Taiwan Normal University, No. 88, Section. 4, Tingzhou Rd. Taipei, 11677, ROC (Taiwan), Fax: (+886) 2-29324249
    • Department of Chemistry, National Taiwan Normal University, No. 88, Section. 4, Tingzhou Rd. Taipei, 11677, ROC (Taiwan), Fax: (+886) 2-29324249

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Abstract

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Tri without fail: The highly diastereoselective addition of vinylaluminum reagents, generated in situ from the zirconium-catalyzed carboalumination of various alkynes and Me3Al, to the easily accessible (2S,5R,6R)-5,6-dimethyl-[1,4]dioxane-2-carbaldehyde (1 b) afforded the corresponding trisubstituted allylic alcohols, and a subsequent Overman reaction yielded allylic amines that contain chiral quaternary carbon stereocenters.

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