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Acetone promoted 1,4-migration of an alkoxycarbonyl group on a syn-1,2-diamine.

Tetrahedron Letters 2017 Februrary 16
A 2-protected cis-amino mitosene undergoes an irreversible acetone promoted isomerization and converts to the 1-isomer. Kinetic studies and DFT calculations of the reaction are reported. An organocatalytic mechanism is proposed, involving a covalent intermediate formed by reaction of the mitosene and acetone.

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