Partial Kinetic 'Resolution' Resulting from a Deuterium Isotope Effect

DOI: 10.1039/c39910000801

Source and publish data:

Journal of the Chemical Society. Chemical communications p. 801 - 802 (1991)

Update date:2022-08-05

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Authors:

Anastasis, Panayiotis

Duffin, Raymond

Gilmore, Christopher

Overton, Karl

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Article abstract of DOI:10.1039/c39910000801

The 'racemate' 1A/1B cyclises on heating to the enol 5 via an 'ene' reaction; at two-thirds completion, the recovered enone 1A/1B has <α>_D -62 deg (1B has <α>_D -132 deg); kinetic 'resolution' results from a deuterium isotope effect for the cyclization (k_H/k_D ca. 1.8); the absolute stereochemistry of compound 6a is determined by X-ray analysis.

Full text of DOI:10.1039/c39910000801

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