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Synfacts 2010(12): 1403-1403
DOI: 10.1055/s-0030-1258850
DOI: 10.1055/s-0030-1258850
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereospecific Suzuki Coupling with Inversion of Stereoconfiguration
Rezensent(en):Paul Knochel, Tobias ThalerT. Ohmura*, T. Awano, M. Suginome*
Kyoto University, Japan
Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration
J. Am. Chem. Soc. 2010, 132: 13191-13193
Kyoto University, Japan
Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration
J. Am. Chem. Soc. 2010, 132: 13191-13193
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. November 2010 (online)
Key words
stereospecificity - Suzuki cross-coupling - Csp³-Csp² coupling - palladium
Significance
This article reports on the Suzuki-Miyaura coupling of enantioenriched α-(acylamino)benzylboronic acid that surprisingly proceeds with inversion of stereoconfiguration.
Comment
Strong intramolecular coordination of the carbonyl group to boron is considered responsible for the preferred backside attack of the palladium complex on the benzylic carbon atom.