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Asymmetric autocatalysis: triggered by chiral isotopomer arising from oxygen isotope substitution.

Angewandte Chemie (International ed. in English) (2011-07-16)
Tsuneomi Kawasaki, Yasushi Okano, Etsuharu Suzuki, Shizuka Takano, Shotaro Oji, Kenso Soai
ABSTRACT

Trigger happy: chiral oxygen isotopomers of hydrobenzoin ([(18)O](R)-1 and [(18)O](S)-1) acted as chiral triggers to induce the enantioselective addition of iPr(2)Zn to pyrimidine-5-carbaldehyde. An extremely small chiral influence arising from the presence of the oxygen isotope ((18)O) is amplified through asymmetric autocatalysis to enantioenrich the 5-pyrimidyl alkanol product.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Benzoin, 98%
Sigma-Aldrich
Benzoin, purified by sublimation, ≥99.5%

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