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Enantioselective Photochemical Organocascade Catalysis.

ABSTRACT: Reported herein is a photochemical cascade process that combines the excited-state and ground-state reactivity of chiral organocatalytic intermediates. This strategy directly converts racemic cyclopropanols and ?,?-unsaturated aldehydes into stereochemically dense cyclopentanols with exquisite stereoselectivity. Mechanistic investigations have enabled elucidating the origin of the stereoconvergence, which is governed by a kinetic resolution process.

SUBMITTER: Wozniak L 

PROVIDER: S-EPMC5814823 | biostudies-other | 2018 Jan

REPOSITORIES: biostudies-other

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Enantioselective Photochemical Organocascade Catalysis.

Woźniak Łukasz Ł   Magagnano Giandomenico G   Melchiorre Paolo P  

Angewandte Chemie (International ed. in English) 20171220 4

Reported herein is a photochemical cascade process that combines the excited-state and ground-state reactivity of chiral organocatalytic intermediates. This strategy directly converts racemic cyclopropanols and α,β-unsaturated aldehydes into stereochemically dense cyclopentanols with exquisite stereoselectivity. Mechanistic investigations have enabled elucidating the origin of the stereoconvergence, which is governed by a kinetic resolution process. ...[more]