Chiral quaternary phosphonium salts as phase-transfer catalysts for environmentally benign asymmetric transformations
作者： Shiyao Liu , Yusuke Kumatabara , Seiji Shirakawa
DOI: 10.1039/C5GC02692J
关键词: Enantioselective synthesis 、 Salt (chemistry) 、 Phase (matter) 、 Catalysis 、 Organic chemistry 、 Organic synthesis 、 Green chemistry 、 Cinchona 、 Phosphonium 、 Chemistry
摘要: Phase-transfer catalysis has been recognized as a powerful and green sustainable method for organic synthesis in both industry academia. Since the pioneering studies on enantioselective phase-transfer reactions promoted by cinchona alkaloid-derived tetraalkylammonium salt catalysts, this research field served an attractive area pursuit of chemistry. Although various types chiral quaternary ammonium salts have developed highly selective asymmetric last three decades, examples phosphonium onium catalysts are limited, effective relatively recent years. This review summarizes development related environmentally benign transformations.
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sci-hub.se 参考文章(67)
Lijia Wang, Seiji Shirakawa, Keiji Maruoka, Asymmetric Neutral Amination of Nitroolefins Catalyzed by Chiral Bifunctional Ammonium Salts in Water-Rich Biphasic Solvent† Angewandte Chemie. ,vol. 50, pp. 5327- 5330 ,(2011) , 10.1002/ANIE.201101307
Seiji Shirakawa, Keiji Maruoka, Recent Developments in Asymmetric Phase-Transfer Reactions Angewandte Chemie. ,vol. 52, pp. 4312- 4348 ,(2013) , 10.1002/ANIE.201206835
Quan Lan, Xisheng Wang, Rongjun He, Changhua Ding, Keiji Maruoka, Highly efficient asymmetric amination of β-keto esters catalyzed by chiral quaternary ammonium bromides Tetrahedron Letters. ,vol. 50, pp. 3280- 3282 ,(2009) , 10.1016/J.TETLET.2009.02.041
Daisuke Uraguchi, Yusuke Ueki, Takashi Ooi, Chiral tetraaminophosphonium carboxylate-catalyzed direct Mannich-type reaction. Journal of the American Chemical Society. ,vol. 130, pp. 14088- 14089 ,(2008) , 10.1021/JA806311E
Fangrui Zhong, Xiaowei Dou, Xiaoyu Han, Weijun Yao, Qiang Zhu, Yuezhong Meng, Yixin Lu, Chiral phosphine catalyzed asymmetric Michael addition of oxindoles. Angewandte Chemie. ,vol. 52, pp. 943- 947 ,(2013) , 10.1002/ANIE.201208285
Daisuke Uraguchi, Natsuko Kinoshita, Daisuke Nakashima, Takashi Ooi, Chiral ionic Brønsted acid–achiral Brønsted base synergistic catalysis for asymmetric sulfa-Michael addition to nitroolefins Chemical Science. ,vol. 3, pp. 3161- 3164 ,(2012) , 10.1039/C2SC20698F
Barry Lygo, Benjamin I. Andrews, Asymmetric Phase-Transfer Catalysis Utilizing Chiral Quaternary Ammonium Salts: Asymmetric Alkylation of Glycine Imines Accounts of Chemical Research. ,vol. 37, pp. 518- 525 ,(2004) , 10.1021/AR030058T
Chuan-Le Zhu, Fa-Guang Zhang, Wei Meng, Jing Nie, Dominique Cahard, Jun-An Ma, Enantioselective Base‐Free Electrophilic Amination of Benzofuran‐2(3H)‐ones: Catalysis by Binol‐Derived P‐Spiro Quaternary Phosphonium Salts Angewandte Chemie. ,vol. 50, pp. 5869- 5872 ,(2011) , 10.1002/ANIE.201100283
Shigeru Arai, Riichiro Tsuji, Atsushi Nishida, Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from l-tartrate Tetrahedron Letters. ,vol. 43, pp. 9535- 9537 ,(2002) , 10.1016/S0040-4039(02)02415-2
Daisuke Uraguchi, Natsuko Kinoshita, Tomohito Kizu, Takashi Ooi, Synergistic Catalysis of Ionic Brønsted Acid and Photosensitizer for a Redox Neutral Asymmetric α-Coupling of N-Arylaminomethanes with Aldimines. Journal of the American Chemical Society. ,vol. 137, pp. 13768- 13771 ,(2015) , 10.1021/JACS.5B09329