Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigat...

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Bibliographic Details
Published inOrganic letters Vol. 21; no. 24; pp. 10164 - 10168
Main Authors Hostmann, Theresa, Molloy, John J, Bussmann, Kathrin, Gilmour, Ryan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.12.2019
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CATALYSIS
STRATEGY
STEREODIVERGENT SYNTHESIS
CHIRAL POOL
ISOMERIZATION
ASYMMETRIC HYDROGENATION
ENANTIOSELECTIVE CONJUGATE REDUCTION
NITROALKENES
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Summary:Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04263