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

被引：13

作者：

Ikeda, Shoma ^{[1
]}

Takeda, Ryohei ^{[1
]}

Fujie, Takaya ^{[1
]}

Ariki, Naoto ^{[1
]}

Nagata, Yuuya ^{[1
,2
]}

Suginome, Michinori ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Synthet Chem & Biol Chem, Nishikyo Ku, Kyoto 6158510, Japan

[2] Hokkaido Univ, Inst Chem React Design & Discovery WPI ICReDD, Kita Ku, Kita 21,Nishi 10, Sapporo, Hokkaido 0010021, Japan

来源：

CHEMICAL SCIENCE | 2021年 / 12卷 / 25期

关键词：

SOLDIERS-TYPE POLY(QUINOXALINE-2,3-DIYL)S; SUZUKI-MIYAURA REACTION; MAIN-CHAIN; STEREOREGULAR POLY((4-CARBOXYPHENYL)ACETYLENE); ENANTIOSELECTIVE SYNTHESIS; SELECTIVE REFLECTION; ASYMMETRIC-SYNTHESIS; AMPLIFICATION; MECHANISM; POLYMERS;

D O I：

10.1039/d1sc01764k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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(-l) 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.

引用

页码：8811 / 8816

页数：6

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