A Planar-Chiral Pillar[5]arene-Based Monophosphine Ligand with Induced Chirality at the Biaryl Axis

被引：10

作者：

Nagata, Yuuya ^{[1
]}

Shimada, Yasuo ^{[2
]}

Nishikawa, Tsuyoshi ^{[1
]}

Takeda, Ryohei ^{[1
]}

Uno, Makoto ^{[1
]}

Ogoshi, Tomoki ^{[2
,3
]}

Suginome, Michinori ^{[1
]}

机构：

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

[2] Kanazawa Univ, Grad Sch Nat Sci & Technol, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

[3] Kanazawa Univ, WPI Nano Life Sci Inst NanoLSI, Kakuma Machi, Kanazawa, Ishikawa 9201192, Japan

来源：

SYNLETT | 2018年 / 29卷 / 16期

关键词：

pillar[5]arene; planar chirality; circular dichroism; chiral ligand; HELICAL POLYMER; CATALYST; PQXPHOS; MOP;

D O I：

10.1055/s-0037-1610635

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A planar-chiral pillar[5]arene with cyclohexylmethoxy side chains and a pendant diphenylphosphine was prepared and used as a chiral ligand in asymmetric reactions. Chirality transfer from the planar-chiral pillar[5]arene scaffold to the chiral biaryl moiety was demonstrated by circular dichroism (CD) spectroscopy, single-crystal X-ray diffraction analysis, and asymmetric catalysis.

引用

页码：2167 / 2170

页数：4

共 23 条

[1] Asymmetric Suzuki-Miyaura cross-coupling of 1-bromo-2-naphthoates using the helically chiral polymer ligand PQXphos
Akai, Yuto
Konnert, Laure
Yamamoto, Takeshi
Suginome, Michinori
[J]. CHEMICAL COMMUNICATIONS, 2015, 51 (33) : 7211 - 7214
[2] Enhanced Catalyst Activity and Enantioselectivity with Chirality-Switchable Polymer Ligand PQXphos in Pd-Catalyzed Asymmetric Silaborative Cleavage of meso-Methylenecyclopropanes
Akai, Yuto
Yamamoto, Takeshi
Nagata, Yuuya
Ohmura, Toshimichi
Suginome, Michinori
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (27) : 11092 - 11095
[3] Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies
Hayashi, T
Hirate, S
Kitayama, K
Tsuji, H
Torii, A
Uozumi, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) : 1441 - 1449
[4] Chiral monodentate phosphine ligand MOP for transition metal-catalyzed asymmetric reactions
Hayashi, T
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) : 354 - 362
[5] Pillar[5]arene-Based Organometallic Cross-Linked Polymer: Synthesis, Structure Characterization, and Catalytic Activity in the Suzuki-Miyaura Coupling Reaction
Liu, Yuezhou
Lou, Baohui
Shangguan, Liqing
Cai, Jingsong
Zhu, Huangtianzhi
Shi, Bingbing
[J]. MACROMOLECULES, 2018, 51 (04) : 1351 - 1356
[6] Supramolecular phosphate transfer catalysis by pillar[5]arene
Liz, Daiane G.
Manfredi, Alex M.
Medeiros, Michelle
Montecinos, Rodrigo
Gomez-Gonzalez, Borja
Garcia-Rio, Luis
Nome, Faruk
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (15) : 3167 - 3170
[7] STEREOISOMERISM AND LOCAL CHIRALITY
MISLOW, K
SIEGEL, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (11) : 3319 - 3328
[8] para-bridged symmetrical pillar[5]arenes:: Their Lewis acid catalyzed synthesis and host-guest property
Ogoshi, Tomoki
Kanai, Suguru
Fujinami, Shuhei
Yamagishi, Tada-aki
Nakamoto, Yoshiaki
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (15) : 5022 - 5023
[9] Chiral supramolecular polymers consisting of planar-chiral pillar[5]arene enantiomers
Ogoshi, Tomoki
Furuta, Takuya
Yamagishi, Tada-aki
[J]. CHEMICAL COMMUNICATIONS, 2016, 52 (71) : 10775 - 10778
[10] Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry
Ogoshi, Tomoki
Yamagishi, Tada-aki
Nakamoto, Yoshiaki
[J]. CHEMICAL REVIEWS, 2016, 116 (14) : 7937 - 8002

← 1 2 3 →