Synthesis of δ-lactones from 2-alkynyl epoxides and 4-alkynyl-1,3-dioxolan-2-ones by palladium catalysed carbonylation and conjugate nucleophilic addition

Autor:	Julian G. Knight, Carl A. Baxter, Simon J. Harwood, Timothy P. Eastman, Simon W. Ainge
Rok vydání:	2000
Předmět:	Sodium borohydride chemistry.chemical_compound Nucleophilic addition Chemistry Organic chemistry chemistry.chemical_element Stereoselectivity Lithium Carbonylation Palladium Conjugate
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :3188-3190
ISSN:	1364-5463 1470-4358
DOI:	10.1039/b006927m
Popis:	Palladium catalysed carbonylation of both 4-alkynyl-1,3-dioxolan-2-ones and alkynyl epoxides occurs under mild conditions to give methyl 5-hydroxy-2,3-dienoates which are converted to γ,δ-unsaturated δ-lactones by tandem conjugate addition–cyclisation with lithium dimethylcuprate or to methyl (E)-5-hydroxypent-3-enoates by stereoselective reduction with sodium borohydride.
Databáze:	OpenAIRE
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