Download PDF
Synfacts 2014; 10(3): 0284
DOI: 10.1055/s-0033-1340694
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Asymmetric Monoborylation of Alkenylsilanes by Copper Catalysis

Contributor(s):
Hisashi Yamamoto
,
Yusuke Ano
Kubota K, Yamamoto E, Ito H * Hokkaido University, Sapporo, Japan
Regio- and Enantioselective Monoborylation of Alkenylsilanes Catalyzed by an Electron-Donating Chiral Phosphine–Copper(I) Complex.

Adv. Synth. Catal. 2013;
355: 3527-3531
CrossrefSearch in Google Scholar
Further Information

Publication History

Publication Date:
17 February 2014 (online)

 
 PDF Download Permissions and Reprints

Key words

copper - borylation - alkenylsilanes

Significance

Chiral organoboron compounds are important building blocks due to their potential for stereospecific transformations. Ito and co-workers describe the copper(I)-catalyzed enantio­selective synthesis of chiral vicinal borosilanes, which are applicable to the stepwise transformation of the boron and silicon functionalities.


#

Comment

The monoborylation of (E)-alkenylsilanes under the standard conditions was successful and proceeded with good enantioselectivity. The alkenylsilane approaches the copper–BenzP* complex in such a way as to minimize the steric repulsion between the silyl substituent and the t-Bu group of the chiral BenzP* ligand. This provides a rational for the high enantioselectivity observed in the C–B bond-forming step.


#
#


   Permissions and Reprints