Protected Amino Acids As a Nonbonding Source of Chirality in Induction of Single-handed Screw-sense to Helical Macromolecular Catalysts

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jul 14

PMID 34257881

Authors

Shoma Ikeda

Ryohei Takeda

Takaya Fujie

Naoto Ariki

Yuuya Nagata

Michinori Suginome

Affiliations

Soon will be listed here.

Abstract

Chiral nonbonding interaction with -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 per monomer unit for the -helical structure over the -helix in -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 (). Use of 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.

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