ArticleOrganic letters2016
Asymmetric Protonation of Cumulenolates: Synthesis of Allenyl Aldehydes Facilitated by an Organomanganese Auxiliary.
Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.
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Who cites it
5 citing papers in PubMed.
- Chiral Allenylcarbonyls - Underexploited Building Blocks for Complex Synthesis.Letters in organic chemistry · 2022Article
- Stereoselective Synthesis of Allenyl Alcohols by Cobalt(III)-Catalyzed Sequential C-H Bond Addition to 1,3-Enynes and Aldehydes.Angewandte Chemie (International ed. in English) · 2022Article
- Carbon-Carbon Bond Formation Facilitated by π-Complexed Organometallic Auxiliaries: An Overview.Letters in organic chemistry · 2019Article
- Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts.Tetrahedron letters · 2017Article
- Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines.Journal of the American Chemical Society · 2016Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
Chiral ammonium salts were used to catalyze the isomerization of organomanganese-complexed alkynyl aldehydes to chiral allenal building blocks in moderate to good enantiomeric excesses. Normally, conjugated alkynyl aldehydes do not isomerize to their thermodynamically less stable allene isomers. However, with a manganese auxiliary in place to promote allene formation, asymmetric protonation of cumulenolate intermediates was realized using a variety of cinchonidinium salts in a weakly basic biphasic reaction system. Optimal results were realized using a novel cinchonidinium geranyl derivative with its C-9 hydroxyl group playing a crucial role in enantioselectivity.
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