Highly Enantioselective Imine Cinnamylation with a Remarkable Diastereochemical Switch

详细信息    查看全文

• 作者：John D. Huber ; James L. Leighton
• 刊名：Journal of the American Chemical Society
• 出版年：2007
• 出版时间：November 28, 2007
• 年：2007
• 卷：129
• 期：47
• 页码：14552 - 14553
• 全文大小：78K
• 年卷期：v.129,no.47(November 28, 2007)
• ISSN：1520-5126

文摘

The first general method for the enantioselective cinnamylation of aldimines is reported. The method utilizes a simple chiral cinnamylsilane reagent and is characterized by experimental simplicity and extraordinarily high levels of enantioselectivity. Further, a remarkable and unprecedented diastereochemical reversal has been realized whereby either diastereomer may be accessed from the same trans-cinnamylsilane based upon a subtle change to the imine, thus obviating the usual requirement for both the trans- and cis-cinnamylsilanes.