Structure tuning of lithium amide for asymmetric 1,4-addition to cinnamate and subsequent demasking |
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| Authors: | Takeo Sakai |
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| Institution: | Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan |
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| Abstract: | Systematic structure tuning of lithium amides derived from benzyl-N-TMS-, allyl-N-TBDMS-, and diisopropylamines lead to several candidates including anthracen-9-ylmethanamine which provided high performance in the enantioselective 1,4-addition (91% ee) and following hydrogenolysis with 10% Pd/C-H2 in methanol to afford β-amino ester. |
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| Keywords: | Asymmetric conjugate addition Lithium amide Chiral ligand Hydrogenolysis Amino acid |
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