Stereoselectivity of formation of monoterpene - Amino acids hybrid molecules in the reaction of monoterpene nitroso chlorides with α-amino acid derivatives

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• 作者：K.S. Marenin^a ; ^{demol@nioch.nsc.ru} ; Yu.V. Gatilov^a ; A.M. Agafontsev^a ; A.V. Tkachev^a ; ^b
• 关键词：Amino acids ; (+)-3-Carene ; (&minus ; )-α-Pinene ; Nitroso chlorides ; Diastereoselectivity
• 刊名：Steroids
• 出版年：2017
• 出版时间：January 2017
• 年：2017
• 卷：117
• 期：Complete
• 页码：112-119
• 全文大小：574 K
• 卷排序：117

文摘

Reaction of nitrosochlorides of natural monoterpene hydrocarbons (+)-3-carene and (−)-α-pinene with L-amino acids and their methyl esters results in stereoselective formation of terpene–amino acids hybrids, which belong to the series of α-substituted amino oximes. The reaction with an excess of racemic DL-amino acids and their derivatives induces partial resolution of the amino acid components and formation of the diastereomeric mixtures of the terpene–amino acids hybrids, with diastereomeric excess varying from 0 to 100%.