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

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 race...

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Veröffentlicht in:Steroids 2017-01, Vol.117, p.112-119
Hauptverfasser: Marenin, K.S., Gatilov, Yu.V., Agafontsev, A.M., Tkachev, A.V.
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container_title Steroids
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creator Marenin, K.S.
Gatilov, Yu.V.
Agafontsev, A.M.
Tkachev, A.V.
description 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%.
doi_str_mv 10.1016/j.steroids.2016.09.016
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source MEDLINE; Elsevier ScienceDirect Journals
subjects (+)-3-Carene
(−)-α-Pinene
Amino acids
Amino Acids - chemistry
Diastereoselectivity
Magnetic Resonance Spectroscopy
Monoterpenes - chemistry
Nitroso chlorides
Stereoisomerism
Terpenes - chemistry
title 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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