Mechanistic investigation leads to a synthetic improvement in the hydrolytic kinetic resolution of terminal epoxides |
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Authors: | Nielsen Lars P C Stevenson Christian P Blackmond Donna G Jacobsen Eric N |
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Institution: | Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. |
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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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