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Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst.

ABSTRACT: A 3-step asymmetric approach toward the optically active chiral cyclohex-2-enones from anisoles has been developed. The crucial asymmetric induction step is an unprecedented catalytic enantioselective isomerization of ?,?-unsaturated cyclohex-3-en-1-ones to the corresponding ?,?-unsaturated chiral enones. This new asymmetric transformation was realized by cooperative iminium-base catalysis with an electronically tunable new organic catalyst. The synthetic utility of this methodology is highlighted by the enantioselective total synthesis of (-)-isoacanthodoral.

SUBMITTER: Lee JH

PROVIDER: S-EPMC3492513 | biostudies-literature | 2012 Nov

REPOSITORIES: biostudies-literature

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Asymmetric approach toward chiral cyclohex-2-enones from anisoles via an enantioselective isomerization by a new chiral diamine catalyst.

Lee Jung Hwa JH Deng Li L

Journal of the American Chemical Society 20121022 44

A 3-step asymmetric approach toward the optically active chiral cyclohex-2-enones from anisoles has been developed. The crucial asymmetric induction step is an unprecedented catalytic enantioselective isomerization of β,γ-unsaturated cyclohex-3-en-1-ones to the corresponding α,β-unsaturated chiral enones. This new asymmetric transformation was realized by cooperative iminium-base catalysis with an electronically tunable new organic catalyst. The synthetic utility of this methodology is highlight ...[more]

PMID: 23043531

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