Atroposelective Arene-Forming Wittig Reaction by Phosphorus P III /P V =O Redox Catalysis

The Wittig reaction is renowned as exceptionally versatile method for converting a diversity of aldehydes and ketones into alkenes. Recently, strategies for chiral phosphine catalysis under P /P =O redox cycling emerged to render this venerable transformation stereoselective. Herein, we describe tha...

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Bibliographic Details
Published inAngewandte Chemie International Edition Vol. 63; no. 37; p. e202408159
Main Authors Jana, Kalipada, Zhao, Zhengxing, Musies, Janis, Sparr, Christof
Format Journal Article
LanguageEnglish
Published Germany 09.09.2024
Subjects
Wittig reaction
phosphines
atropisomers
endogenous base
arene formation
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Summary:The Wittig reaction is renowned as exceptionally versatile method for converting a diversity of aldehydes and ketones into alkenes. Recently, strategies for chiral phosphine catalysis under P /P =O redox cycling emerged to render this venerable transformation stereoselective. Herein, we describe that phosphine redox catalysis enables the enantioselective synthesis of pertinent biaryl atropisomers by means of a stereocontrolled arene-forming Wittig reaction. Key to the process is the release of an endogenous base from readily accessible tert-butyloxycarbonylated Morita-Baylis-Hillman adducts triggered by catalyst intramolecularization, permitting mild phosphine redox catalysis for atroposelective Wittig reactions. By this strategy, a broad diversity of biaryl atropisomers is obtained with up to 94 : 6 enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.202408159