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Asymmetric autocatalysis: product recruitment for the increase in the chiral environment (PRICE)

Journal

CHEMICAL SOCIETY REVIEWS
Volume 31, Issue 4, Pages 211-222

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b104169j

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Asymmetric catalytic reactions are possible vas efficient transfer of the chiral environment of reaction to the transition state. In theory any asymmetric structure may contribute to this, including the product of the reaction itself. For product influence to be significant, a nonlinear effect needs to operate, whereby one diastereomer of the product/catalyst assists the reaction, and the other does not: When these conditions are satisfied, we obtain an asymmetric autocatalytic reaction in: which the enantiomeric excess of a compound,(that is both product and. catalyst). actually increases-as the reaction iterates: It is only recently that we have seen reports of such processes. Of particular. interest are Soai's reports of the,alkylation of aromatic heterocycles. Such, reactions, aside from their inherent. interest, may offer clues into the origins of asymmetric molecular replication that predated the origin of life.

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