From Amino Acids to Fused Chiral Pyrrolidines and Piperidines via the INOC Route

Autor:	Abraham Nudelman, Hugo E. Gottlieb, Eliezer Falb, Alfred Hassner
Rok vydání:	2000
Předmět:	chemistry.chemical_classification chemistry.chemical_compound Olefin fiber Nitrile chemistry Stereochemistry Intramolecular force Organic Chemistry Oxide Physical and Theoretical Chemistry Cycloaddition Amino acid
Zdroj:	European Journal of Organic Chemistry. 2000:645-655
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(200002)2000:4<645::aid-ejoc645>3.0.co;2-i
Popis:	Intramolecular nitrile oxide olefin cycloaddition (INOC) reactions of oximes 1–3 and of 24–27 derived from L-amino acids have been found to proceed stereoselectively, yielding tricyclic fused pyrrolidines and piperidines. Further manipulation led to chiral hydroxymethyl-substituted fused piperidines 33–35 and to 3-amino-4-(1-hydroxypropyl)-2-mercaptomethyl-N-methylpiperidine (36). The structures and stereochemistries of the fused systems, as well as those of the piperidines, have been established by NMR.
Databáze:	OpenAIRE
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