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Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

ABSTRACT: We report a dynamic kinetic resolution (DKR) of chiral 4-pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate ?,?-disubstituted cyclopentanones with high enantio- and diastereoselectivities.

SUBMITTER: Chen Z

PROVIDER: S-EPMC6501835 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Dynamic Kinetic Resolution of Aldehydes by Hydroacylation.

Chen Zhiwei Z Aota Yusuke Y Nguyen Hillary M H HMH Dong Vy M VM

Angewandte Chemie (International ed. in English) 20190227 14

We report a dynamic kinetic resolution (DKR) of chiral 4-pentenals by olefin hydroacylation. A primary amine racemizes the aldehyde substrate via enamine formation and hydrolysis. Then, a cationic rhodium catalyst promotes hydroacylation to generate α,γ-disubstituted cyclopentanones with high enantio- and diastereoselectivities. ...[more]

PMID: 30740841

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