Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

to related objects

Abstract: The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes ; volume:131 ; number:1 ; year:2019 ; pages:179-183 ; extent:5
Angewandte Chemie ; 131, Heft 1 (2019), 179-183 (gesamt 5)

Creator: Demming, Rebecca M.
Hammer, Stephan C.
Nestl, Bettina M.
Gergel, Sebastian
Fademrecht, Silvia
Pleiss, Jürgen
Hauer, Bernhard

DOI: 10.1002/ange.201810005

URN: urn:nbn:de:101:1-2022070712202262890874

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:39 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Show original at data provider

Associated

Demming, Rebecca M.
Hammer, Stephan C.
Nestl, Bettina M.
Gergel, Sebastian
Fademrecht, Silvia
Pleiss, Jürgen
Hauer, Bernhard

Other Objects (12)

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Hochschulschrift

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Electroreduction of unactivated alkenes using water as hydrogen source

Electroreduction of unactivated alkenes using water as hydrogen source

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Hochschulschrift

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Electroreduction of unactivated alkenes using water as hydrogen source

Electroreduction of unactivated alkenes using water as hydrogen source

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Radical‐Mediated Hydroperfluoroalkylation of Unactivated Alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Metal-free electrochemical dihydroxylation of unactivated alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Iridium-Catalyzed Asymmetric Hydroalkynylation of Unactivated Alkenes

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Hochschulschrift

Photoinduced nickel-catalyzed oxyarylation/amidoarylation of unactivated alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Electrochemical Rearrangement for Remote Functionalizations of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Nickel-Catalyzed anti-Markovnikov Hydroarylation of Unactivated Alkenes

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Intramolecular Hydroacylation of Unactivated Alkenes by NHC Catalysis

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Radical 1‐Fluorosulfonyl‐2‐alkynylation of Unactivated Alkenes

Electroreduction of unactivated alkenes using water as hydrogen source

Electroreduction of unactivated alkenes using water as hydrogen source

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

Enzymatic Aerobic Oxidation of Aliphatic Alkenes to Aldehydes: Directed Evolution, Mechanistic Studies, and Application in Synthesis

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

EPOXIDATION OF ALIPHATIC ALKENES BY DIMETHYLDIOXIRANE: STERIC EFFECTS

Cultural heritage institutions wishing to register will find more information here.

Fields marked * need to be filled in.

Username*

Please enter your username

Email*

Please enter your email address

Please do not fill this field

First name

Last name

Password*

Please enter your password

Confirm password*

Please enter the same password

I have read the terms of use and the privacy policy for the collection of personal data and accept them. *

This field is required.

I would like to subscribe to the newsletter of the Deutsche Digitale Bibliothek. See newsletter subscription info.

Account created

Your "My DDB" account has been successfully created. Before you can log in to your account, you must click the confirmation link in the message we just sent to the email address you provided.