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Enantioselective 5-exo-Fluorocyclization of Ene-Oximes.

ABSTRACT: The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.

SUBMITTER: Rouno T

PROVIDER: S-EPMC6804199 | biostudies-literature | 2019 Sep

REPOSITORIES: biostudies-literature

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Enantioselective 5-exo-Fluorocyclization of Ene-Oximes.

Rouno Taiki T Niwa Tomoki T Nishibashi Kousuke K Yamamoto Nobuharu N Egami Hiromichi H Hamashima Yoshitaka Y

Molecules (Basel, Switzerland) 20190924 19

The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline. ...[more]

PMID: 31554247

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