First Evidence for the Formation of a Geminal Dizinc Carbenoid:  A Highly Stereoselective Synthesis of 1,2,3-Substituted Cyclopropanes

Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variet...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 124; no. 3; pp. 386 - 387
Main Authors Charette, André B, Gagnon, Alexandre, Fournier, Jean-François
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.01.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Cyclopropanes - chemical synthesis
Exact sciences and technology
Kinetics and mechanisms
Organic chemistry
Physical Sciences
Reactivity and mechanisms
Science & Technology
Stereoisomerism
HALIDES
REACTIVITY
ZINC REAGENTS
ORGANOBISMETALLIC REAGENTS
CYCLIC STEREOCONTROL
Zinc Organic compounds
Cyclopropanation
Reaction intermediate
Stereoselectivity
Organic free biradical
Carbenoid
Experimental study
Ethylenic compound
Primary alcohol
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Summary:Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variety of electrophiles. 1,2,3-Substituted cyclopropane derivatives are formed with excellent diastereoselectivities by using this simple procedure.
Bibliography:ark:/67375/TPS-JSWM3J6C-Z
istex:D71BD95C608798A758EDB9666714E9EF53ED390D
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja017230d