Synfacts 2009(6): 0650-0650  
DOI: 10.1055/s-0029-1217154
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Rhodium-Catalyzed Asymmetric 1,4-Addition of Heteroaryl Triolborates

Contributor(s): Mark Lautens, Praew Thansandote
X.-Q. Yu, Y. Yamamoto*, N. Miyaura*
Hokkaido University, Sapporo, Japan
Further Information

Publication History

Publication Date:
25 May 2009 (online)


The authors describe a rhodium-catalyzed asymmetric 1,4-addition of pyridyl and thiophenyl triolborates to α,β-unsaturated carbonyl compounds. The scope is good for neutral and electron-rich heteroaryl triolborates and cyclic and acyclic enones. When the heteroatom is adjacent to the triolborate, only traces of product are seen except if ortho-blocking groups are present.