The Tethered Aminohydroxylation (TA) of Cyclic Allylic Carbamates

详细信息    查看全文

• 作者：Timothy J. Donohoe ; Peter D. Johnson ; Andrew Cowley ; and Martine Keenan
• 刊名：Journal of the American Chemical Society
• 出版年：2002
• 出版时间：November 6, 2002
• 年：2002
• 卷：124
• 期：44
• 页码：12934 - 12935
• 全文大小：72K
• 年卷期：v.124,no.44(November 6, 2002)
• ISSN：1520-5126

文摘

The tethered aminohydroxylation of cyclic allylic carbamates is described using catalytic amounts of potassium osmate. The mechanism of reaction involves formation of an imido-osmium complex which adds intramolecularly to alkenes with complete control of both regio- and stereoselectivity: the formation of syn-aminodiol motifs is now straightforward using this chemistry. Proof of the mechanism was obtained with an X-ray crystal structure of an azaglycolate osmate ester intermediate.