Tandem cross metathesis and intramolecular aza-Michael reaction to synthesize bicyclic piperidines and indolizidine 167E

Autor:	Jhih-Liang Huang, Shang-Shing P. Chou
Rok vydání:	2012
Předmět:	Bicyclic molecule Stereochemistry Organic Chemistry Indolizidine Metathesis Biochemistry chemistry.chemical_compound chemistry Intramolecular force Drug Discovery Michael reaction Aza-Diels–Alder reaction Stereoselectivity Piperidine
Zdroj:	Tetrahedron Letters. 53:5552-5554
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2012.08.031
Popis:	We have successfully transformed the terminal alkenes of dihydropyridones to the α,β-unsaturated esters by cross metathesis (CM). After detosylation the secondary amides can undergo the intramolecular aza-Michael reaction to give the bicyclic piperidine structures. The stereoselectivity of the aza-Michael reaction is determined by the size of the newly formed ring. With simple transformations we have also achieved the synthesis of indolizidine 167E.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2d3fee35c3ed2d2e5a474b18cc1658ce https://doi.org/10.1016/j.tetlet.2012.08.031 Zobrazit plný text záznamu Full Text from ScienceDirect