An Efficient Entry to Optically Active anti- and syn--Amino- 详细信息    查看全文

• 作者：Santos Fustero ; Laia Albert ; José ; Luis Aceñ ; a ; Juan F. Sanz-Cervera ; Amparo Asensio
• 刊名：Organic Letters
• 出版年：2008
• 出版时间：February 21, 2008
• 年：2008
• 卷：10
• 期：4
• 页码：605 - 608
• 全文大小：90K
• 年卷期：v.10,no.4(February 21, 2008)
• ISSN：1523-7052

文摘

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The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF₃ in the presence of a suitable activator leads to trifluoromethyl lactols,which can be selectively reduced to anti--amino--trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when thestarting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF₃ group in the lactolintermediates has been observed. This represents a formal CF₃ addition to the imine function in the starting substrates.