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<p>The first <i>P</i>*,<i>P</i>-bidentate ligand of the 2,6-dioxa-7-aza-1-phosphabicyclo[2.2.1]heptane series possessing a rigid <i>P</i>-chiral phosphoramidite framework and an additional phosphine donor center in a side substituent was synthesized. A <i>cis</i>-bis-chelate complex containing two molecules of a phosphino dialkyl phosphite derivative of this ligand was obtained. The use of the new <i>P</i>*,<i>P</i>-ligand as a chiral inducer in Pd-catalyzed asymmetric allylic alkylation of (<i>E</i>)-1,3-diphenylallyl acetate with dimethyl malonate and cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate provided <i>ee</i> of up to 46% and 53%, respectively.</p>

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First P*,P-bidentate ligand with a chiral bicyclic phosphoramidite framework

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • I. V. Chuchelkin,
  • A. I. Lukankov,
  • V. K. Gavrilov,
  • I. D. Firsin,
  • E. S. Rud,
  • D. A. Fedorov,
  • K. N. Gavrilov

摘要

The first P*,P-bidentate ligand of the 2,6-dioxa-7-aza-1-phosphabicyclo[2.2.1]heptane series possessing a rigid P-chiral phosphoramidite framework and an additional phosphine donor center in a side substituent was synthesized. A cis-bis-chelate complex containing two molecules of a phosphino dialkyl phosphite derivative of this ligand was obtained. The use of the new P*,P-ligand as a chiral inducer in Pd-catalyzed asymmetric allylic alkylation of (E)-1,3-diphenylallyl acetate with dimethyl malonate and cinnamyl acetate with ethyl 2-oxocyclohexane-1-carboxylate provided ee of up to 46% and 53%, respectively.