1,4-Bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines in Synthesis. Highly Regio- and Stereoselective SN1′ and Alkylation Reactions

Autor:	Donald Craig, Raymond McCague, Gerard A. Potter, Meredith R. V. Williams
Rok vydání:	1998
Předmět:	chemistry.chemical_compound chemistry Nucleophile Organic Chemistry Stereoselectivity Piperidine Aziridine Alkylation Medicinal chemistry Sulfone
Zdroj:	Synlett. 1998:55-57
ISSN:	1437-2096 0936-5214
Popis:	Reaction of lithiated β-sulfonyl acetals with amino acid-derived N-tosylaziridines followed by acid-catalysed cyclisation gives enantiomerically pure 2-alkyl 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydropyridines 3 in good yields. These heterocyclic substrates react efficiently and highly stereoselectively with a range of carbon nucleophiles under Lewis acidic conditions to give the 1,2,5,6-tetrahydropyridine products of SN1′ reaction, and undergo lithiation followed by completely stereoselective reaction at the 4-position with haloalkanes.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::91fa3986d89296160411c933feba56a9 https://doi.org/10.1055/s-1998-1566 Zobrazit plný text záznamu