New atropoisomeric alkenylphenylglycine derivatives: Synthesis of (5R*)- and (5S*)-isomers of (1R*,3aR*,4S*,11S*)-3a,5,9,11-tetramethyl-4,5-dihydro-3aH-1,4-methano[1,3]oxazolo[3,2-a]quinolin-2-one

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• 作者：Guliya G. Bizhanova^a ; Kyrill Yu. Suponitsky^b ; Yulia V. Vakhitova^c ; Rail R. Gataullin^a ; ^{gataullin@anrb.ru}
• 关键词：[3+2]-cycloaddition ; Alkenylaniline ; Aromatic amino Claisen rearrangement ; Atropisomerism ; Ketene ; Mü ; nchnone ; Methanooxazoloquinoline
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：12 January 2017
• 年：2017
• 卷：73
• 期：2
• 页码：109-115
• 全文大小：930 K
• 卷排序：73

文摘

We synthesized methyl ester of N-(1-methylbut-2-en-1-yl)-N-phenylglycine which underwent acid catalyzed aromatic amino Claisen rearrangement to provide methyl-N-[2-(1-methylbut-2-en-1-yl)phenyl]glycinate. A mixture of syn- and anti-atropisomeric methyl-N-acetyl-N-[4-methyl-2-(1-methylbut-2-en-1-yl)phenyl]glycinates was obtained either by the reaction of this ester with acetyl bromide or by the reaction of the sodium salt of N-acetyl-2-(1-methylbut-2-en-1-yl)-4-methylaniline with methyl bromoacetate. Upon saponification of the synthesized ester mixture the syn-atropisomer of N-acetyl-N-[4-methyl-2-(1-methylbut-2-en-1-yl)phenyl]glycine was isolated by fractional crystallization. Treatment of the obtained acids with acetic anhydride, ethyl chloroformate, dicyclohexylcarbodiimide or isopropenylacetate leads to compounds of 4,5-dihydro-3aH-methano[1,3]oxazolo[3,2-a]quinolin-2-one structure.