817166-12-4

Usage

Structure

It is a cyclic organic compound with a furan ring and a carbonyl group, combined with an ethoxy and ethyl substituent.

Classification

Lactone

Stereochemistry

(6R,6aR) based on the IUPAC nomenclature system

Uses

Building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile chemical reactivity and ability to serve as a precursor for various functional groups.

Upstream product

• 368-39-8 triethyloxonium fluoroborate 
• 102998-71-0 4-iodo-1-ethylbut-1-yne 

Relevant academic research and scientific papers

Interaction of dihydropyridines and nucleophiles with carbene complexes of chromium: Diastereo- and enantioselective synthesis of polycyclic butenolides

The interaction of N-methyldihydropyridine with carbene complexes of chromium promotes their spontaneous homologation upon addition of a hydride to the carbene carbon and an insertion of CO. This is followed in the case of complexes tethered to a triple bond by cascade insertions of the triple bond and of a CO ligand giving finally butenolides. The scope of the reaction has been established with its limitations, together with the stereochemical outcome, which is discussed. [5.5], [5.6], [5.7] bicyclic and tricyclic systems have been synthesised together with chiral butenolides starting from chiral carbene complexes. Most of the new structures have been assessed by X-ray crystallography. This transformation was first extended to dihydronicotinamides, to chiral dihydropyridines such as dihydronicotines which led to the butenolides in an enantioselective way, and to other sources of hydrides. Second, a series of nucleophiles such as alkoxides, alkyllithium and alkylmagnesium compounds led also to polycyclic, substituted butenolides. Moreover, the final lactone enolates could be trapped with oxygen and gave unsaturated lactonols. The key point in all of these reactions is the formation of tetrahedral intermediates upon interaction of the nucleophiles with the carbene carbon. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Linear coupling of three CO ligands of chromium hexacarbonyl leading to functionalized butenolides via fischer carbene complexes

Up to the three CO ligands of [Cr(CO)6] can be incorporated in a linear fashion as functional groups of butenolides via alkanyl(alkoxy)carbene complexes of chromium. The key step is the biomimetic reduction of the carbene group with N-methyl dihydropyridine [Eq.(1)], which induces the cascade insertions of the triple bond and of two CO groups.

A major breakthrough in the use of alkoxycarbene complexes of chromium and tungsten for the synthesis of elaborate organic compounds: Dihydropyridine induced reductions and cascade insertion reactions

Alkoxy (alkyl)carbene complexes of tungsten and chromium react with dihydropyridine and N-methyldihydropyridine to give respectively pyridinium ylid complexes and N-methylpyridinium tungstates and chromates. These two types of complexes can be used, for the former, as cyclopropanation reagents, for the latter, as unprecedented initiators of cascade multiinsertions of olefins, alkynes and CO. These insertions lead to elaborate polycyclic compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.