Helix-Sense-Selective and Enantiomer-Selective Living Polymerization of Phenyl Isocyanide Induced by Reusable Chiral Lactide Using Achiral Palladium Initiator

  • Chen J
  • Yang L
  • Wang Q
 et al. 
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Abstract

Polymerization of phenyl isocyanide using achiral Pd(II) initiator with the presence of chiral l- or d-lactide (l-LA or d-LA) as additive was found to proceed in helix-sense-selective manner. The polymerization of achiral phenyl isocyanide, 4-isocyanobenzoyl-2-aminoisobutyric acid decyl ester (1) by this method produced optically active helical poly-1m(L), whose chirality was solely come from the helical conformation without containing of any other chiral atoms. The added chiral LA can be facilely recovered and reused in the helix-sense-selective polymerizations without significantly loss of its chiral induction, and the chiral economy of the polymerization is high. When enantiomerically pure phenyl isocyanide bearing an R- or S-alanine pendent with a long n-decyl chain (1r or 1s) were polymerized by this method, the polymerization was found to proceed in a highly enantiomer-selective manner with one of the enantiomers preferentially polymerized over the antipode by a factor of 3.6. Single-handed helical polyisocyanides can be achieved when the chirality of the monomer was appropriately matched with the added LA.
Polymerization of phenyl isocyanide using achiral Pd(II) initiator with the presence of chiral l- or d-lactide (l-LA or d-LA) as additive was found to proceed in helix-sense-selective manner. The polymerization of achiral phenyl isocyanide, 4-isocyanobenzoyl-2-aminoisobutyric acid decyl ester (1) by this method produced optically active helical poly-1m(L), whose chirality was solely come from the helical conformation without containing of any other chiral atoms. The added chiral LA can be facilely recovered and reused in the helix-sense-selective polymerizations without significantly loss of its chiral induction, and the chiral economy of the polymerization is high. When enantiomerically pure phenyl isocyanide bearing an R- or S-alanine pendent with a long n-decyl chain (1r or 1s) were polymerized by this method, the polymerization was found to proceed in a highly enantiomer-selective manner with one of the enantiomers preferentially polymerized over the antipode by a factor of 3.6. Single-handed helical polyisocyanides can be achieved when the chirality of the monomer was appropriately matched with the added LA.

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Authors

  • Jia Li Chen

  • Li Yang

  • Qian Wang

  • Zhi Qiang Jiang

  • Na Liu

  • Jun Yin

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