Photopolymerization in chiral crystals. 3. Toward an "absolute" asymmetric synthesis of optically active dimers and polymers with quantitative enantiomeric yield

1979 ◽  
Vol 101 (8) ◽  
pp. 2152-2156 ◽  
Author(s):  
Lia Addadi ◽  
Meir Lahav
Keyword(s):  
Asymmetric Synthesis ◽  
Optically Active ◽  
Absolute Asymmetric Synthesis ◽  
Chiral Crystals

Absolute Asymmetric Synthesis by Nucleophilic Carbonyl Addition Using Chiral Crystals of Achiral Amides.

ChemInform ◽  
2004 ◽  
Vol 35 (36) ◽  
Author(s):  
Masami Sakamoto ◽  
Shuichiro Kobaru ◽  
Takashi Mino ◽  
Tsutomu Fujita
Keyword(s):  
Asymmetric Synthesis ◽  
Absolute Asymmetric Synthesis ◽  
Carbonyl Addition ◽  
Chiral Crystals

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.

Sign in / Sign up

Export Citation Format

Share Document