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Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals via stereospecific C-F bond cleavage.

ABSTRACT: The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst 1. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding α-hydroxyacetals in a stereospecific manner. Accordingly, the one-pot conversion of α-branched aldehydes into α-hydroxyacetals was achieved for the first time in high enantioselectivity.

SUBMITTER: Shibatomi K

PROVIDER: S-EPMC5975931 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Enantioselective fluorination of α-branched aldehydes and subsequent conversion to α-hydroxyacetals <i>via</i> stereospecific C-F bond cleavage.

Shibatomi Kazutaka K Kitahara Kazumasa K Okimi Takuya T Abe Yoshiyuki Y Iwasa Seiji S

Chemical science 20151116 2

The highly enantioselective fluorination of α-branched aldehydes was achieved using newly developed chiral primary amine catalyst <b>1</b>. Furthermore, the C-F bond cleavage of the resulting α-fluoroaldehydes proceeded smoothly under alcoholic alkaline conditions to yield the corresponding α-hydroxyacetals in a stereospecific manner. Accordingly, the one-pot conversion of α-branched aldehydes into α-hydroxyacetals was achieved for the first time in high enantioselectivity. ...[more]

PMID: 29910896

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