Preparation of chiral allenylmetal reagents from enantioenriched allenyl iodides and propargylic mesylates. A comparison of indium, bismuth, and tin derivatives

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8214-8219

  Marshall, James A ^a   Grant, Charsetta M ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH DERIVATIVE; INDIUM; IODINE DERIVATIVE; MESYLIC ACID DERIVATIVE; TIN DERIVATIVE;

ARTICLE; CHIRALITY; MOLECULAR INTERACTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033615512     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990938e     Document Type: Article

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30. f = 0.5-0.6 appears on the TLC plate. This spot is the dppf ligand resulting from decomposition of the catalyst. In such cases, the procedure is best terminated. If the reaction stops without appearance of the ligand, it can be restarted with additional InI. The premature termination appears to be related to the quality of the InI powder. When this problem is encountered with a particular batch of InI, the use of 9:1 THF-HMPA as solvent and 10 mol % catalyst is recommended in subsequent applications of the procedure.