Enantiospecific Photochemical Norrish/Yang Type II Reaction of Nonbiaryl Atropchiral α-Oxoamides in Solution—Axial to Point Chirality Transfer

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• 作者：Anoklase Jean-Luc Ayitou ; Josepha L. Jesuraj ; Nilotpal Barooah ; Angel Ugrinov ; J. Sivaguru
• 刊名：Journal of the American Chemical Society
• 出版年：2009
• 出版时间：August 19, 2009
• 年：2009
• 卷：131
• 期：32
• 页码：11314-11315
• 全文大小：141K
• 年卷期：v.131,no.32(August 19, 2009)
• ISSN：1520-5126

文摘

α-Oxoamides 1 with o-tert-butyl substitution on the N-phenyl moiety were found to be stable axially chiral atropisomers. These axially chiral α-oxoamides undergo enantiospecific photochemical γ-Hydrogen abstraction in CHCl₃ to yield β-lactams with high enantioselectivity (e.r. 90:10) in solution. The extent of enantioselectivity was found to be dependent on the reaction temperature.