In conclusion, the chiral diamines 5 and 7, derived from
Cinchona alkaloids and thus accessible from inexpensive
commercially available materials, efficiently desymmetrise
meso-1,2-diols. On screening conditions, THF or EtOAc
emerged as the best solvents, giving highly enantioenriched
monobenzoate at low temperature with low 2 mol% catalyst
loadings.
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Notes and references
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¨
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z 4 and 6 are also commercially available from Aldrich and from
Buchler GmbH, Braunschweig, Germany.
y When using diamines 5 and 7 as catalysts in CH2Cl2, the diamine
solution should be prepared and rapidly cooled to 4 ꢀ20 1C.
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ꢁc
This journal is The Royal Society of Chemistry 2008
Chem. Commun., 2008, 3519–3521 | 3521