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Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels-Alder Reactions of Cyclohexadienones with Cyclopentadiene.

ABSTRACT: We describe a highly enantioselective Diels-Alder reaction of cross-conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of stereoselectivity.

SUBMITTER: Ghosh S

PROVIDER: S-EPMC7383742 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels-Alder Reactions of Cyclohexadienones with Cyclopentadiene.

Ghosh Santanu S Das Sayantani S De Chandra Kanta CK Yepes Diana D Neese Frank F Bistoni Giovanni G Leutzsch Markus M List Benjamin B

Angewandte Chemie (International ed. in English) 20200311 30

We describe a highly enantioselective Diels-Alder reaction of cross-conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of ...[more]

PMID: 32159921

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