NDLI: Ether solvent-induced chirality inversion of helical poly(quinoxaline-2,3-diyl)s containing l-lactic acid derived side chains

Content Provider	Royal Society of Chemistry (RSC)
Author	Takagi, Keisuke Nagata, Yuuya Kuroda, Takuma Suginome, Michinori
Copyright Year	2014
Abstract	Poly(quinoxaline-2,3-diyl)s containing (S)-1-(alkoxycarbonyl)ethoxymethyl side chains derived from natural L-lactic acid were synthesized to investigate the induction of single-handed helical chirality of the main chain. In ether solvents, the handedness of the helical chirality of the polymer main chain is crucially dependent on the length of the alkyl chain in the lactate alkoxy groups. A polymer bearing pentyl ester groups showed an effective solvent-dependent helix inversion between 1,2-dimethyxyethane (1,2-DME, M-Helix) and tert-butyl methyl ether (MTBE, P-Helix). A single-handed copolymer bearing both the pentyl lactate moieties and diphenylphosphino groups was prepared to use as a chiral ligand in an asymmetric Suzuki–Miyaura coupling reaction. The chirality of the ligand could be inverted by the choice of solvents (1,2-DME or MTBE) resulting in the production of either R- or S-enantiomers with high enantiomeric excesses.
Starting Page	4953
Ending Page	4956
Page Count	4
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	5
Issue Number	12
Journal	Chemical Science
DOI	10.1039/c4sc01920b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Quinoxaline Methyl tert-butyl ether Miyaura Ether Ligand Axial chirality Butyl group Polymer Dimethoxyethane Ester Carboxylic acid Alkyl Chirality Suzuki Lactic acid Copolymer Chiral ligand Coupling reaction
Content Type	Text
Resource Type	Article
Subject	Chemistry

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