Rhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives
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)
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
Peer-reviewed publications
Work outside EPFL
Journal Articles
Published
Record creation date
2011-08-17