Soai reaction

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In organic chemistry, the Soai reaction is the alkylation of pyrimidine-5-carbaldehyde with diisopropylzinc. The reaction is autocatalytic and leads to rapidly increasing amounts of the same enantiomer of the product. The product pyrimidyl alcohol is chiral and induces that same chirality in further catalytic cycles. Starting with a low enantiomeric excess produces a product with very high enantiomeric excess.[1] The reaction has been studied for clues about the origin of homochirality among certain classes of biomolecules.

Soai autocatalysis.png

The Japanese chemist Kenso Soai (1950–) discovered the reaction in 1995.[2] For his work in "elucidating the origins of chirality and homochirality", Soai received the Chemical Society of Japan award in 2010.[3]

Other chiral additives can be used as the initial source of asymmetric induction, with the major product of that first reaction being rapidly amplified.[4]

Cryptochirality autocatalysis.png

References[edit]

  1. ^ Flügel, Rolf M. (January 11, 2011). Chirality and Life: A Short Introduction to the Early Phases of Chemical Evolution. Springer. pp. 16–17. ISBN 9783642169779. 
  2. ^ Shibata, Takanori; Morioka, Hiroshi; Hayase, Tadakatsu; Choji, Kaori; Soai, Kenso (1996). "Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol". Journal of the American Chemical Society. 118: 471. doi:10.1021/ja953066g. 
  3. ^ "CSJ Award 2010: Prof. Kenso Soai". Retrieved 2015-04-14. 
  4. ^ Kawasaki, T.; Tanaka, H.; Tsutsumi, T.; Kasahara, T.; Sato, I.; Soai, K. (2006). "Chiral Discrimination of Cryptochiral Saturated Quaternary and Tertiary Hydrocarbons by Asymmetric Autocatalysis". J. Am. Chem. Soc. 128 (18): 6032–6033. PMID 16669661. doi:10.1021/ja061429e. 

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