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 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%.
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 630090 Novosibirsk, Russian Federation. Electronic address: demol@nioch.nsc.ru.
K S
KS
Marenin
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 630090 Novosibirsk, Russian Federation.
Yu V
YV
Gatilov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 630090 Novosibirsk, Russian Federation.
A M
AM
Agafontsev
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 630090 Novosibirsk, Russian Federation; Department of Natural Sciences, Novosibirsk State University, 630090 Novosibirsk, Russian Federation.
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Tkachev
D000596:Amino Acids / Q000737:chemistry*; D000081008:Bicyclic Monoterpenes; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000737:chemistry*; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry
D000596:Amino Acids; D000081008:Bicyclic Monoterpenes; D039821:Monoterpenes; D013729:Terpenes; C030218:3-carene; C005451:alpha-pinene
(+)-3-Carene; (−)-α-Pinene; Amino acids; Diastereoselectivity; Nitroso chlorides