Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
Abstract: The combination of small‐molecule catalysis and enzyme catalysis represents an underexploited area of research with huge potential in asymmetric synthetic chemistry due to both compatibility of reaction conditions and complementary reactivity. Herein, we describe the telescopic synthesis of chiral nitro alcohols starting from commercially available benzaldehyde derivatives through the one‐pot three‐step chemoenzymatic cascade combination of a Wittig reaction, chiral‐thiourea‐catalysed asymmetric conjugate addition, and ketoreductase‐mediated reduction to access the corresponding target compounds in moderate to excellent overall isolated yields (36–80 %) and high diastereomeric and enantiomeric ratios (up to >97: 3). This represents the first example of the combination of an organocatalysed asymmetric conjugate addition via iminium ion activation and a bioreduction step catalysed by ketoreductases.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols ** ; day:05 ; month:09 ; year:2022 ; extent:1
Angewandte Chemie / International edition. International edition ; (05.09.2022) (gesamt 1)
- Creator
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Ascaso‐Alegre, Christian
Herrera, Raquel P.
Mangas‐Sánchez, Juan
- DOI
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10.1002/anie.202209159
- URN
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urn:nbn:de:101:1-2022090515254483292898
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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15.08.2025, 7:30 AM CEST
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Associated
- Ascaso‐Alegre, Christian
- Herrera, Raquel P.
- Mangas‐Sánchez, Juan
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Modern biocatalysis : stereoselective and environmentally friendly reactions
Stereoselective Synthesis of syn-Homoallylic Alcohols
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Stereoselective Three‐Step One‐Pot Cascade Combining Amino‐ and Biocatalysis to Access Chiral γ‐Nitro Alcohols **
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Stereoselective Synthesis of syn-Homoallylic Alcohols
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Streamlined One‐Pot Synthesis of Nitro Fatty Acids
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Enantioselective biocatalysis for the preparation of optically pure tertiary alcohols
A facile, stereoselective, one-pot synthesis of resveratrol derivatives