Ligand-accelerated enantioselective propargylation of aldehydes via allenylzinc reagents

Organic Letters

Volumn 13, Issue 8, 2011, Pages 1900-1903

  Trost, Barry M ^a   Ngai, Ming Yu ^a   Dong, Guangbin ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; ALLENE; LIGAND; PROPANE; ZINC;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

ALDEHYDES; ALKADIENES; LIGANDS; MOLECULAR STRUCTURE; PROPANE; STEREOISOMERISM; ZINC;

EID: 79955443801     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200043n     Document Type: Article

References (34)

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31. After screening awide range of arene additives,wwere able to restore the reaction conversion and selectivity by addition of 150 mol% naphthalene. Howver, the homopropargyl alcohol productWs accompaniedwith 15% ethyl transfer byproduct. More studies are underWy to examine the exact role of an arene additive in this transformation.
32. The proposed dinuclear-zinc mechanism is based on thewelldeveloped aminoalcohol catalyzed asymmetric dialkyl- and diarylzinc addition to aldehydes,
33. see ref 11. One of the referees suggested a mononuclear-zinc mechanism, which cannot be ruled out at this stage.
34. The reaction does not show nonlinear effects (see Supporting Information), so a single Zn-complex is depicted in the proposed reaction mechanism.