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Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis.

ABSTRACT: The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

SUBMITTER: Sarie JC

PROVIDER: S-EPMC7496101 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis.

Sarie Jérôme C JC Thiehoff Christian C Neufeld Jessica J Daniliuc Constantin G CG Gilmour Ryan R

Angewandte Chemie (International ed. in English) 20200609 35

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF<sub>2</sub> enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manif ...[more]

PMID: 32347605

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