Simple generation of nonstabilized azomethine ylides through decarboxylative condensation of α-amino acids with carbonyl compounds via 5-oxazolidinone intermediates
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In this paper, the α-amino acids with a variety of carbonyl compounds are used to generate azomethine ylides of nonstabilized types through the elimination of water and carbon dioxide.Abstract:
Heating α-amino acids with a variety of carbonyl compounds generates N-unsubstituted or N-substituted azomethine ylides of nonstabilized types through the elimination of water and carbon dioxide. The ylides are captured by olefinic, acetylenic, and carbonyl dipolarophiles producing pyrrolidines, pyrrolines, and oxazolidines. The reaction involves intermediary 5-oxazolidinones which can be sometimes isolated. Some synthetic equivalents of parent azomethine ylide, methaniminium methylide, are accessible by this route.read more
Citations
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Book ChapterDOI
Recent Advances in Azomethine Ylide Chemistry
Otohiko Tsuge,Shuji Kanemasa +1 more
TL;DR: Azomethine ylides are planar molecules composed of one nitrogen and two terminal sp2 carbons at most four geometrical isomers are possible for these transient molecules Their cycloadditions to olefin or acetylene dipolarophiles give rise to the formation of two sets of carbon-carbon bonds in a single step as discussed by the authors.
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Chiral catalysts in the stereoselective synthesis of pyrrolidine derivatives via metallo-azomethine ylides
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1,3-dipolar cycloaddition reactions of porphyrins with azomethine ylides.
Ana M. G. Silva,Augusto C. Tomé,Maria G. P. M. S. Neves,and Artur M. S. Silva,José A. S. Cavaleiro +4 more
TL;DR: Mixed isobacteriochlorin derivatives were prepared from the reaction of azomethine ylides with the chlorin monoadducts previously obtained via Diels-Alder reactions.
References
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Journal ArticleDOI
Trifluoroacetic Acid-Catalyzed 1, 3-Cycloaddition of the Simplest Iminium Ylide Leading to 3-or 3, 4-Substituted Pyrrolidines and 2, 5-Dihydropyrroles
TL;DR: The 1, 3-dipolar cycloaddition of an intermediary iminium ylide formed from N-benzyl-N-(methoxymethyl) trimethylsilylmethylamine to conjugated olefinic and acetylenic dipolarophiles in the presence of a catalytic amount of trifluoroacetic acid has been found to give 3 or 3, 4-substituted pyrrolidines and 2, 5-dihydropyrroles.
Journal ArticleDOI
Synthetic application of cyanoaminosilanes as azomethine ylide equivalents
Journal ArticleDOI
Diastereofacial selectivity in azomethine ylide cycloaddition reactions derived from chiral α-cyanoaminosilanes
TL;DR: In this paper, the extent of diastereoselectivity associated with the 1,3-dipolar cycloaddition of chiral azomethine ylides with dipolarophiles has been studied.
Journal ArticleDOI
Evidence for an azomethine ylide intermediate in the carbonyl- assisted decarboxylation of sarcosine. Novel synthesis of dl-phenylephrine hydrochloride
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