Stereochemistry of Cyanide Ion Addition to 3,4,5,6-Tetrahydropyridinium Derivatives

M. Y.H. Essawi; P. S. Portoghese

doi:10.1021/jo00161a004

Stereochemistry of Cyanide Ion Addition to 3,4,5,6-Tetrahydropyridinium Derivatives

M. Y.H. Essawi, P. S. Portoghese

Medicinal Chemistry

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Abstract

The stereochemistry of cyanide ion addition to l-alkyl-4-(iV-phenylpropanamido)-3,4,5,6-tetrahydropyridinium salts 2 was investigated by analysis of the 1H NMR spectra of the isolated α-amino nitriles. The data obtained, together with epimerization studies, indicated that the addition occurred in a stereospecific manner to afford the trans diastereoisomers.

Original language	English (US)
Pages (from-to)	2138-2140
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	48
Issue number	13
DOIs	https://doi.org/10.1021/jo00161a004
State	Published - Jul 1983

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title = "Stereochemistry of Cyanide Ion Addition to 3,4,5,6-Tetrahydropyridinium Derivatives",

abstract = "The stereochemistry of cyanide ion addition to l-alkyl-4-(iV-phenylpropanamido)-3,4,5,6-tetrahydropyridinium salts 2 was investigated by analysis of the 1H NMR spectra of the isolated α-amino nitriles. The data obtained, together with epimerization studies, indicated that the addition occurred in a stereospecific manner to afford the trans diastereoisomers.",

author = "Essawi, {M. Y.H.} and Portoghese, {P. S.}",

year = "1983",

month = jul,

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pages = "2138--2140",

journal = "Journal of Organic Chemistry",

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AU - Essawi, M. Y.H.

AU - Portoghese, P. S.

PY - 1983/7

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N2 - The stereochemistry of cyanide ion addition to l-alkyl-4-(iV-phenylpropanamido)-3,4,5,6-tetrahydropyridinium salts 2 was investigated by analysis of the 1H NMR spectra of the isolated α-amino nitriles. The data obtained, together with epimerization studies, indicated that the addition occurred in a stereospecific manner to afford the trans diastereoisomers.

AB - The stereochemistry of cyanide ion addition to l-alkyl-4-(iV-phenylpropanamido)-3,4,5,6-tetrahydropyridinium salts 2 was investigated by analysis of the 1H NMR spectra of the isolated α-amino nitriles. The data obtained, together with epimerization studies, indicated that the addition occurred in a stereospecific manner to afford the trans diastereoisomers.

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ER -

Stereochemistry of Cyanide Ion Addition to 3,4,5,6-Tetrahydropyridinium Derivatives

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