Chemistry of ethanediyl S,S-acetals - 4. A promising way to cis-substituted olefins, stereoselectively from carbonyl compounds

Article abstract of DOI:10.1080/00397919208019317

Aldehydes and methyl ketones readily afford 5,6-dihydro-1,4-dithiins that can be converted by n-butyllithium into their corresponding sulfur stabilized carbanions. Coupling of the latter with alkyl halides leads to species having a cis-configurated, disubstituted double bond tied up by the sulfur-containing ring which is known to be susceptible of selective removal.

Full text of DOI:10.1080/00397919208019317

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Synthetic Communications: An
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Chemistry of Ethanediyl S,S-
Acetals - 4. Promising Way
to Cis-Substituted Olefins,
Stereoselectively from
Carbonyl Compounds
Romualdo Caputo a , Carla Ferreri a , Patrizia Isita
a , Luigi Longobardo a , Domenico Mastroianni a
Giovanni Palumbo a
&
a Dipartimento di Chimica Organica , Biologica
dell'Università , Via Mezzocannone, 16 I-80134,
Napoli, Italy
Published online: 24 Sep 2006.
To cite this article: Romualdo Caputo , Carla Ferreri , Patrizia Isita , Luigi
Longobardo , Domenico Mastroianni & Giovanni Palumbo (1992) Chemistry of
Ethanediyl S,S-Acetals - 4. Promising Way to Cis-Substituted Olefins, Stereoselectively
from Carbonyl Compounds, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 22:9, 1345-1350, DOI:
10.1080/00397919208019317
To link to this article: http://dx.doi.org/10.1080/00397919208019317
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