Enantiomer-selective activation of racemic catalysts

Koichi Mikami, Masahiro Terada, Toshinobu Korenaga, Yousuke Matsumoto, Satoru Matsukawa

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Abstract

Asymmetric catalysts can be evolved into highly activated catalysts by association with chiral activators. This asymmetric activation process is particularly useful in racemic catalysis through selective activation of one enantiomer of the racemic catalysts. Recently, a strategy whereby a racemic catalyst is selectively deactivated by a chiral additive has been reported to yield nonracemic products. However, we have reported a strategy that is an alternative to asymmetric catalysts but is conceptually opposite, in which a chiral activator selectively activates rather than deactivates one enantiomer of a racemic chiral catalyst. The advantage of this activation strategy over the deactivation counterpart is that the activated catalyst can produce a greater enantiomeric excess (x(act)% ee) in the products than the ee attained by the enantiomerically pure catalyst on its own. Therefore, 'asymmetric activation' could provide a general and powerful strategy for the use of not only atropisomeric and, hence, racemic ligands but also chirally flexible and 'pro-atropisomeric' ligands without enantiomeric resolution!

Original languageEnglish
Pages (from-to)391-401
Number of pages11
JournalAccounts of Chemical Research
Volume33
Issue number6
DOIs
Publication statusPublished - 2000 Jul 19
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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    Mikami, K., Terada, M., Korenaga, T., Matsumoto, Y., & Matsukawa, S. (2000). Enantiomer-selective activation of racemic catalysts. Accounts of Chemical Research, 33(6), 391-401. https://doi.org/10.1021/ar9900818