The mechanism of an asymmetric ring-opening reaction of epoxide with amine catalyzed by a metal–organic framework: insights from combined quantum mechanics and molecular mechanics calculations

2017 ◽  
Vol 46 (11) ◽  
pp. 3470-3481 ◽  
Author(s):  
Kazuki Doitomi ◽  
Kai Xu ◽  
Hajime Hirao
Keyword(s):  
Quantum Mechanics ◽  
Molecular Mechanics ◽  
Ring Opening ◽  
Metal Organic Framework ◽  
Molecular Mechanics Calculations ◽  
Π Interactions ◽  
Ring Opening Reaction ◽  
Metal Organic ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

QM/MM computations suggest that the asymmetric ring-opening reaction of epoxide with amine is controlled by CH–π interactions between aniline and a naphthol moiety.

scholarly journals Asymmetric ring-opening reaction of meso-epoxides with aromatic amines using homochiral metal–organic frameworks as recyclable heterogeneous catalysts

RSC Advances ◽  
2018 ◽  
Vol 8 (49) ◽  
pp. 28139-28146 ◽  
Author(s):  
Koichi Tanaka ◽  
Maya Kinoshita ◽  
Jun Kayahara ◽  
Yutaro Uebayashi ◽  
Kazusada Nakaji ◽  
...  
Keyword(s):  
Aromatic Amines ◽  
Ring Opening ◽  
Heterogeneous Catalysts ◽  
Metal Organic Framework ◽  
Metal Organic Frameworks ◽  
Amino Alcohols ◽  
Ring Opening Reaction ◽  
Ring Opening Reactions ◽  
Metal Organic ◽  
Asymmetric Ring Opening

Asymmetric ring-opening reactions of meso-epoxides by aromatic amines were achieved by using some chiral metal–organic frameworks. The corresponding β-amino alcohols were obtained with good yields and enantioselectivities (up to 97% ee).

ChemInform Abstract: Enantioselective Ring-Opening Reaction of Epoxides with MeOH Catalyzed by Homochiral Metal-Organic Framework.

ChemInform ◽  
2012 ◽  
Vol 43 (41) ◽  
pp. no-no
Author(s):  
Koichi Tanaka ◽  
Ken-ichi Otani ◽  
Takanori Murase ◽  
Shyota Nishihote ◽  
Zofia Urbanczyk-Lipkowska
Keyword(s):  
Ring Opening ◽  
Metal Organic Framework ◽  
Ring Opening Reaction ◽  
Metal Organic ◽  
Organic Framework

Asymmetric ring-opening of cyclopropyl ketones with β-naphthols catalyzed by a chiral N,N′-dioxide–scandium(iii) complex

2018 ◽  
Vol 5 (8) ◽  
pp. 1293-1296 ◽  
Author(s):  
Yong Xia ◽  
Fenzhen Chang ◽  
Lili Lin ◽  
Yali Xu ◽  
Xiaohua Liu ◽  
...  
Keyword(s):  
Ring Opening ◽  
Complex Catalyst ◽  
Ring Opening Reaction ◽  
Cyclopropyl Ketones ◽  
Naphthol Derivatives ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

An efficient asymmetric ring-opening reaction of cyclopropyl ketones with 2-naphthols has been realized using a chiral N,N′-dioxide–ScIII complex catalyst. A variety of chiral β-naphthol derivatives were obtained in excellent outcomes (up to 99% yield, 97% ee).

ChemInform Abstract: Palladium/Zinc Co-Catalyzed syn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols.

ChemInform ◽  
2015 ◽  
Vol 46 (43) ◽  
pp. no-no
Author(s):  
Sifeng Li ◽  
Jianbin Xu ◽  
Baomin Fan ◽  
Zhiwu Lu ◽  
Chaoyuan Zeng ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

Palladium/Zinc Co-Catalyzedsyn-Stereoselectively Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Phenols

2015 ◽  
Vol 21 (25) ◽  
pp. 9003-9007 ◽  
Author(s):  
Sifeng Li ◽  
Jianbin Xu ◽  
Baomin Fan ◽  
Zhiwu Lu ◽  
Chaoyuan Zeng ◽  
...  
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction

Sidearm as a Control in the Asymmetric Ring Opening Reaction of Donor-Acceptor Cyclopropane

2014 ◽  
Vol 32 (8) ◽  
pp. 669-672 ◽  
Author(s):  
Qikai Kang ◽  
Lijia Wang ◽  
Zhongbo Zheng ◽  
Junfang Li ◽  
Yong Tang
Keyword(s):  
Ring Opening ◽  
Ring Opening Reaction ◽  
Donor Acceptor ◽  
Asymmetric Ring Opening ◽  
Asymmetric Ring Opening Reaction
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