Enantioselective Intermolecular [2 + 2 + 2] Cycloadditions of Ene–Allenes with Allenoates

An enantioselective [2 + 2 + 2] cycloaddition of ene–allenes with allenoates is described, which transforms simple π-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of...

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Bibliographic Details
Published inOrganic letters Vol. 14; no. 23; pp. 6096 - 6099
Main Authors Brusoe, Andrew T, Edwankar, Rahul V, Alexanian, Erik J
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.12.2012
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACETYLENES
CYCLIZATIONS
NICKEL
LIGANDS
NITRILES
COMPLEXES
ISOCYANATES
ALKYNES
DERIVATIVES
DIYNES
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Summary:An enantioselective [2 + 2 + 2] cycloaddition of ene–allenes with allenoates is described, which transforms simple π-components into stereochemically complex carbocycles in a single step. The rhodium(I)-catalyzed cycloaddition proceeds with good levels of enantioselectivity, and with high levels of regio-, chemo-, and diastereoselectivity. Our results are consistent with a mechanism involving an enantioselective intermolecular allene–allene oxidative coupling.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303024q