Iodine-mediated ring-closing iodoamination with concomitant N-debenzylation for the asymmetric synthesis of polyhydroxylated pyrrolidines

Autor:	Rebecca L. Nicholson, Andrew D. Smith, Paul M. Roberts, Stephen G. Davies, Angela J. Russell, Paul D. Price, James E. Thomson, Edward D. Savory
Jazyk:	angličtina
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Stereochemistry Alkene Organic Chemistry Enantioselective synthesis chemistry.chemical_element Ring (chemistry) Iodine Medicinal chemistry Catalysis Inorganic Chemistry chemistry Stereoselectivity Physical and Theoretical Chemistry Retrosynthetic analysis
Zdroj:	TETRAHEDRON-ASYMMETRY. 20(6-8)
ISSN:	1362-511X 0957-4166
Popis:	Treatment of a range of homochiral unsaturated β-amino esters (containing a cis-dioxolane unit) with iodine promotes a novel ring-closing alkene iodoamination reaction which proceeds with concomitant N-debenzylation, providing a simple and stereoselective route to iodomethyl pyrrolidines. Functional group interconversion of the resulting iodomethyl pyrrolidines upon treatment with AgOAc proceeds via the corresponding aziridinium ion, with subsequent deprotection giving access to polyhydroxylated pyrrolidines. © 2009 Elsevier Ltd. All rights reserved.
Databáze:	OpenAIRE
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