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. 2004 Feb 11;126(5):1360-2.
doi: 10.1021/ja038590z.

Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides

Lars P C Nielsen  1 , Christian P Stevenson, Donna G Blackmond, Eric N Jacobsen
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Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides

Lars P C Nielsen et al. J Am Chem Soc. .

Abstract

The mechanism of the hydrolytic kinetic resolution (HKR) of terminal epoxides was investigated by kinetic analysis using reaction calorimetry. The chiral (salen)Co-X complex (X = OAc, OTs, Cl) undergoes irreversible conversion to (salen)Co-OH during the course of the HKR and thus serves as both precatalyst and cocatalyst in a cooperative bimetallic catalytic mechanism. This insight led to the identification of more active catalysts for the HKR of synthetically useful terminal epoxides.

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