Enantioselective Alkenylation and Phenylation Catalyzed by a Chiral CuF Complex

详细信息    查看全文

• 作者：Daisuke Tomita ; Reiko Wada ; Motomu Kanai ; and Masakatsu Shibasaki
• 刊名：Journal of the American Chemical Society
• 出版年：2005
• 出版时间：March 30, 2005
• 年：2005
• 卷：127
• 期：12
• 页码：4138 - 4139
• 全文大小：46K
• 年卷期：v.127,no.12(March 30, 2005)
• ISSN：1520-5126

文摘

A new method for CuF-catalyzed alkenylation and phenylation of aldehydes and an activated ketone using air- and moisture-stable alkenylsilanes and phenylsilane as a nucleophile is described. This methodology was extended to highly enantioselective catalytic alkenylation and phenylation using DTBM-SEGPHOS as a chiral ligand. Substrate generality is broad, and an alkenylsilane with a long alkyl chain and an internal alkenylsilane can be also used as a nucleophile. The key to success partly involves the accelerated regeneration of reactive alkenylcopper and phenylcopper through transmetalation from the silylated nucleophiles, and stabilization of the reactive copper reagents, both of which are effected by the diphosphine ligands.