Publication

Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

Pierre Vogel
1997
Journal Articles

Abstract

The enantiomerically pure (1S,4R,4'S,5'S)-1-(4',5'-dimethyl-dioxolan-2'-yl)-5,6-dimethylidene-7-ox abicyclo[2.2.1 derived from the acetal of furfural and (2S,3S)-butane-2,3-diol underwent addition to 1-acetylvinyl para-nitrobenzoate in the presence of an excess of t-BuMe2SiOSO2CF3 to yield an 83:17 mixture of two diastereomeric products which was converted into (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone. (C) 1997 Elsevier Science Ltd.

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Pierre Vogel
1997
Journal Articles

Abstract

Official source

Related concepts (8)

Enantiomer

In chemistry, an enantiomer (/ɪˈnænti.əmər, ɛ-, -oʊ-/ ih-NAN-tee-ə-mər; from Ancient Greek ἐνάντιος (enántios) 'opposite', and μέρος (méros) 'part') – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are non-superposable onto their own . Enantiomers are much like one's right and left hands, when looking at the same face, they cannot be superposed onto each other. No amount of reorientation in three spatial dimensions will allow the four unique groups on the chiral carbon (see chirality) to line up exactly.

Enantiomeric excess

In stereochemistry, enantiomeric excess (ee) is a measurement of purity used for chiral substances. It reflects the degree to which a sample contains one enantiomer in greater amounts than the other. A racemic mixture has an ee of 0%, while a single completely pure enantiomer has an ee of 100%. A sample with 70% of one enantiomer and 30% of the other has an ee of 40% (70% − 30%). Enantiomeric excess is defined as the absolute difference between the mole fraction of each enantiomer: where In practice, it is most often expressed as a percent enantiomeric excess.

Diastereomer

In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers.

Related publications (2)

Remote control of Diels-Alder additions. Enantioselective synthesis of (2R)-1,2,3,4-tetrahydro-2-hydroxy-5,8-dimethoxynaphthalen-2-yl methyl ketone (Wong's anthracycline intermediate) from furfural

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Synthesis of enantiomerically pure 1,2-diamine derivatives of 7-azabicyclo[2.2.1]heptane. New leads as glycosidase inhibitors and rigid scaffolds for the preparation of peptide analogues

Synthesis of Polypropionate Fragments Containing Tertiary-Alcohol Moieties - Cross-Aldolisations with Lithium Enolates of 7-Oxabicyclo[2.2.1]Heptan-2-One Derivatives