Enantioselective synthesis utilizing enantiomorphous organic crystal of achiral benzils as a source of chirality in asymmetric autocatalysis

Tsuneomi Kawasaki; Yuuki Harada; Kenta Suzuki; Takayuki Tobita; Nicola Florini; Gyula Pályi; Kenso Soai

doi:10.1021/ol801600y

Enantioselective synthesis utilizing enantiomorphous organic crystal of achiral benzils as a source of chirality in asymmetric autocatalysis

Org Lett. 2008 Sep 18;10(18):4085-8. doi: 10.1021/ol801600y. Epub 2008 Aug 23.

Authors

Tsuneomi Kawasaki¹, Yuuki Harada, Kenta Suzuki, Takayuki Tobita, Nicola Florini, Gyula Pályi, Kenso Soai

Affiliation

¹ Department of Applied Chemistry, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601 Japan.

PMID: 18722453
DOI: 10.1021/ol801600y

Abstract

Chiral crystals of achiral benzils act as efficient chiral initiators of asymmetric autocatalysis to afford highly enantioenriched pyrimidyl alkanols whose absolute configurations depend upon the enantiomorph of the crystal used in conjunction with asymmetric autocatalysis with amplification of enantiomeric excess.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Phenylglyoxal / analogs & derivatives*
Phenylglyoxal / chemistry
Pyrimidines / chemical synthesis
Pyrimidines / chemistry
Stereoisomerism
Substrate Specificity

Substances

Pyrimidines
pyrimidine
Phenylglyoxal
benzil