Rhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives
Seiser, Tobias; Cramer, Nicolai
2010

Abstract

Enantioselective Rh-promoted activation and 1,4-positional swap of unactivated tetraorganosilanes, e.g., 1-ethyl-3-methyl-3-(2-(trimethylsilyl)phenyl)cyclobutanol (I) to give (1S,3S)-1-ethyl-3-methyl-3((trimethylsilyl)methyl)indanol (II). E.g., reaction of silylphenyl tert-cyclobutanol I with 2.5 mol% [Rh(cod)OH]2/6.0 mol% (R)-Difluorphos ligand at 100° in mesitylene gave 82% yield of trans-indanol II (97% ee).

Details

Title Rhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives
Author(s) Seiser, Tobias ; Cramer, Nicolai
Published in Angewandte Chemie, International Edition
Volume 49
Issue 52
Pages 10163-10167
Date 2010
Publisher Wiley-VCH Verlag GmbH & Co. KGaA
ISSN 1433-7851
Keywords
Note CAPLUS AN 2010:1580668(Journal)
DOI https://doi.org/10.1002/anie.201005399
Laboratories LCSA
Record Appears in Scientific production and competences > SB - School of Basic Sciences > ISIC - Institute of Chemical Sciences and Engineering > LCSA - Laboratory of Asymmetric Catalysis and Synthesis
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date 2011-08-17

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