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

ABSTRACT: 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.

SUBMITTER: Napolitano T

PROVIDER: S-EPMC5604470 | biostudies-literature | 2017 Feb

REPOSITORIES: biostudies-literature

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

Napolitano Tanya T Cheng Shu-Yuan SY Nielsen Brooke B Choi Christopher C Aguilar William W Paz Manuel M MM Sapse Anne-Marie AM Champeil Elise E

Tetrahedron letters 20170103 7

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. ...[more]

PMID: 28943668

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