Download PDF
Synfacts 2013; 9(1): 0086
DOI: 10.1055/s-0032-1317730
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Direct Amination of Alkyl and Aryl Pinacol Boronates

Contributor(s):
Paul Knochel
,
Nadja M. Barl
Mlynarski SN, Karns AS, Morken JP * Boston College, Chestnut Hill, USA
Direct Stereospecific Amination of Alkyl and Aryl Pinacol Boronates.

J. Am. Chem. Soc. 2012;
134: 16449-16451
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
 PDF Download Permissions and Reprints

Key words

boron - lithium - direct amination - pinacol boronates

Significance

Herein, the direct and stereospecific amination of various aryl and alkyl pinacol boronates with lithiated methoxyamine is disclosed. The corresponding (un)protected amines are obtained in very good yield and, in case of ­chiral compounds, with high enantiomeric excess.


#

Comment

Sensitive functional groups such as CN, OMe and CF3 moieties are well tolerated with this methodology. In addition, this strategy might even be applied to gram-scale reactions without any further drawbacks.


#
#


   Permissions and Reprints