Issue 25, 2021

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

Abstract

Chiral nonbonding interaction with N-protected amino acid methyl esters used as chiral additives in achiral solvents allows dynamic induction of single-handed helical conformation in poly(quinoxaline-2,3-diyl)s (PQX) bearing only achiral substituents. Ac-L-Pro-OMe, for instance, allows induction of energy preference of 0.16 kJ mol−1 per monomer unit for the M-helical structure over the P-helix in t-butyl methyl ether (MTBE). With this new mode of screw-sense induction, homochiral screw-sense has been induced in virtually achiral poly(quinoxaline-2,3-diyl)s 1000-mer containing phosphine pendants (PQXphos). Use of PQXphos as a helically dynamic ligand along with Ac-Pro-OMe (L or D) as a chiral additive in MTBE allowed a highly enantioselective Suzuki–Miyaura coupling reaction with up to 95% enantiomeric excess.

Graphical abstract: Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

Supplementary files

Article information

Article type
Edge Article
Submitted
29 Mar 2021
Accepted
25 May 2021
First published
26 May 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 8811-8816

Protected amino acids as a nonbonding source of chirality in induction of single-handed screw-sense to helical macromolecular catalysts

S. Ikeda, R. Takeda, T. Fujie, N. Ariki, Y. Nagata and M. Suginome, Chem. Sci., 2021, 12, 8811 DOI: 10.1039/D1SC01764K

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