Rhodium(I)-Catalyzed 1,4-Silicon Shift of Unactivated Silanes from Aryl to Alkyl: Enantioselective Synthesis of Indanol Derivatives

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).


Published in:
Angewandte Chemie, International Edition, 49, 52, 10163-10167
Year:
2010
Publisher:
Wiley-VCH Verlag GmbH & Co. KGaA
ISSN:
1433-7851
Keywords:
Note:
CAPLUS AN 2010:1580668(Journal)
Laboratories:




 Record created 2011-08-17, last modified 2018-03-17


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