Highly enantioselective asymmetric autocatalysis of 2-alkenyl- and 2-vinyl-5-pyrimidyl alkanols with significant amplification of enantiomeric excess

Chirality ◽  
2002 ◽  
Vol 14 (2-3) ◽  
pp. 166-168 ◽  
Author(s):  
Itaru Sato ◽  
Tomotaka Yanagi ◽  
Kenso Soai
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

scholarly journals Crystal Structure of the Isopropylzinc Alkoxide of Pyrimidyl Alkanol: Mechanistic Insights for Asymmetric Autocatalysis with Amplification of Enantiomeric Excess

2015 ◽  
Vol 54 (50) ◽  
pp. 15218-15221 ◽  
Author(s):  
Arimasa Matsumoto ◽  
Takaaki Abe ◽  
Atsushi Hara ◽  
Takayuki Tobita ◽  
Taisuke Sasagawa ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Asymmetric autocatalysis of 5-carbamoyl-3-pyridyl alkanols with amplification of enantiomeric excess

2000 ◽  
Vol 11 (21) ◽  
pp. 4249-4253 ◽  
Author(s):  
Shigehisa Tanji ◽  
Yasutaka Kodaka ◽  
Atsushi Ohno ◽  
Takanori Shibata ◽  
Itaru Sato ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Self-Replication and Amplification of Enantiomeric Excess of Chiral Multifunctionalized Large Molecules by Asymmetric Autocatalysis

2014 ◽  
Vol 53 (42) ◽  
pp. 11199-11202 ◽  
Author(s):  
Tsuneomi Kawasaki ◽  
Mai Nakaoda ◽  
Yutaro Takahashi ◽  
Yusuke Kanto ◽  
Nanako Kuruhara ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Large Molecules ◽  
Asymmetric Autocatalysis ◽  
Self Replication

scholarly journals Asymmetric autocatalysis triggered by triglycine sulfate with switchable chirality by the direction of electric field

2021 ◽  
Author(s):  
Tsuneomi Kawasaki ◽  
Yoshiyasu Kaimori ◽  
Seiya Shimada ◽  
Natsuki Hara ◽  
Susumu Sato ◽  
...  
Keyword(s):  
Electric Field ◽  
Organic Compounds ◽  
Enantiomeric Excess ◽  
Triglycine Sulfate ◽  
Molecular Chirality ◽  
Asymmetric Autocatalysis ◽  
Soai Reaction

Triglycine sulfate (TGS) acts as a chiral trigger for asymmetric autocatalysis with amplification of enantiomeric excess, i.e., the Soai reaction. Therefore, molecular chirality of highly enantioenriched organic compounds is controlled...

ChemInform Abstract: Asymmetric Autocatalysis of 5-Carbamoyl-3-pyridyl Alkanols with Amplification of Enantiomeric Excess.

ChemInform ◽  
2001 ◽  
Vol 32 (14) ◽  
pp. no-no
Author(s):  
Shigehisa Tanji ◽  
Yasutaka Kodaka ◽  
Atsushi Ohno ◽  
Takanori Shibata ◽  
Itaru Sato ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Relationship between the time, yield, and enantiomeric excess of asymmetric autocatalysis of chiral 2-alkynyl-5-pyrimidyl alkanol with amplification of enantiomeric excess

2003 ◽  
Vol 14 (8) ◽  
pp. 975-979 ◽  
Author(s):  
Itaru Sato ◽  
Daisuke Omiya ◽  
Hiroyoshi Igarashi ◽  
Keiichi Kato ◽  
Yoshihiro Ogi ◽  
...  
Keyword(s):  
Enantiomeric Excess ◽  
Asymmetric Autocatalysis

Absolute Asymmetric Synthesis: A Commentary

2003 ◽  
Vol 68 (5) ◽  
pp. 849-864 ◽  
Author(s):  
Kurt Mislow
Keyword(s):  
Asymmetric Synthesis ◽  
Enantiomeric Excess ◽  
Optically Active ◽  
Random Chance ◽  
Chemical Reagents ◽  
Absolute Asymmetric Synthesis ◽  
Asymmetric Autocatalysis ◽  
Physical Forces ◽  
Biomolecular Homochirality ◽  
The Difference

Absolute asymmetric synthesis, i.e., the formation of enantiomerically enriched products from achiral precursors without the intervention of chiral chemical reagents or catalysts, is in practice unavoidable on statistical grounds alone. That random chance, combined with suitable amplification mechanisms, might ultimately account for biomolecular homochirality in Nature was recognized more than a century ago. Soai and collaborators have recently developed an asymmetric autocatalysis reaction that is capable of amplifying a tiny enantiomeric excess of far below 1% to yield a nearly enantiopure product. Although there is no easy way to tell the difference between an asymmetric autocatalysis reaction initiated by the tiny enantiomeric excess due to random chance and one initiated by minuscule quantities of unidentified chiral impurities, it is nevertheless all but certain that the Soai reaction is capable of producing optically active compounds by an absolute asymmetric synthesis, starting from nominally achiral reagents free of chiral contaminants and run under achiral conditions, e.g., without the intervention of chiral physical forces.

Circular Dichroism Spectroscopy of Catalyst Preequilibrium in Asymmetric Autocatalysis of Pyrimidyl Alkanol

2021 ◽  
Author(s):  
Arimasa Matsumoto ◽  
Ayame Tanaka ◽  
Yoshiyasu Kaimori ◽  
Natsuki Hara ◽  
Yuji Mikata ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Spectrum Analysis ◽  
Circular Dichroism Spectrum ◽  
Unique Feature ◽  
Enantiomeric Excess ◽  
Circular Dichroism Spectroscopy ◽  
Asymmetric Autocatalysis ◽  
Mechanistic Understanding ◽  
Circular Dichroïsm

Mechanistic understanding of asymmetric autocatalysis of pyrimidyl alkanol is highly attracting and challenging topic due to its unique feature of amplification of enantiomeric excess. Circular dichroism spectrum analysis of this...

Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule

Nature ◽  
1995 ◽  
Vol 378 (6559) ◽  
pp. 767-768 ◽  
Author(s):  
Kenso Soai ◽  
Takanori Shibata ◽  
Hiroshi Morioka ◽  
Kaori Choji
Keyword(s):  
Enantiomeric Excess ◽  
Chiral Molecule ◽  
Asymmetric Autocatalysis
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