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DOI: 10.1055/s-0030-1258807
Asymmetric Conjugate Addition of Arylboronic Acids to Nitroolefins
Contributor(s):Hisashi Yamamoto, Patrick BradyShanghai Institute of Organic Chemistry and Shanghai Institute of Materia Medica, P. R. of China
Rhodium-Catalyzed Asymmetric Conjugate Addition of Organoboronic Acids to Nitroalkenes Using Chiral Bicyclo[3.3.0] Diene Ligands
Angew. Chem. Int. Ed. 2010, 49: 5780-5783
Publication History
Publication Date:
21 October 2010 (online)
Key words
nitroolefins - conjugate addition - arylboronic acids - rhodium
Significance
This report describes conjugate addition to nitroolefins with high yields and good to excellent enantioselectivities. This method overcomes the previously described difficulties in controlling enantioselectivity for substrates lacking α-substituents.
Comment
The inclusion of water and KHF2 is believed to improve the catalyst turnover. The authors also propose that KHF2 may react with the arylboronic acid to generate the aryltrifluoroborate, which may undergo transmetalation to generate the arylrhodium intermediate. The enantioselectivity in this report ranges from good to excellent. We anticipate seeing further improvements.