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Stereoselective synthesis of and atropisomerism in 4-pyridyl-3-(1-pyridinio)-3,4-trans-1,2,3,4-tetrahydropyridines and their transformation products

✍ Scribed by Anatolij M. Shestopalov; Olga P. Bogomolova; Ludmila A. Rodinovskaja; Victor P. Litvinov; Bogdan Bujnicki; Marian Mikol̀ajczyk; Vladimir N. Nesterov; Yurij T. Struchkov

Publisher: John Wiley and Sons
Year: 1993
Tongue: English
Weight: 893 KB
Volume: 4
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.520040612

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✦ Synopsis

A series of 2-oxo4pyrrdyll-3-(l -pyrrdinio)-5-cyano-3,4trans-l,2,3,4-tetrahydropyridine-6-olates were prepared by condensation of pyridinium ylides with a$unsaturated carbonyl compounds or more conveniently by a three-component condensation of pyridiniurn ylides, pyridine aldehydes, and ethyl cyanoacetate 3 and/or 6. This analogues of the above tetrahydropyridines were prepared in a similar way starting from suitable substrates. Spectroscopic data rmeuled that the reaction leads to trans-isomers around the C3-c* bond and is atroposelective. The conformation of and tautomerism in the tetrahydropyridines are discussed in the light of ' H NMR data. The reaction of 5-cyano-3-(3-methyl-l-pyridinio)-2-0~0-4-(3-pyridyl)-l,2,3,4-tetrahydropyridine-6-thiolate 1Oc with *To whom correspondence should be addressed.

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