Catalytic scaffolding ligands: An efficient strategy for directing reactions

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9210-9211

  Lightburn, Thomas E ^a   Dombrowski, Michael T ^a   Tan, Kian L ^a  

^a BOSTON COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; SCAFFOLD PROTEIN;

ARTICLE; CATALYSIS; CHEMICAL REACTION;

EID: 47749098988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja803011d     Document Type: Article

References (34)

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28. In the Supporting Information, a more detailed discussion of the synthesis is presented.
29. 31P NMR analysis showed a minor compound (∼3%) which we have assigned as the minor syn-diastereomer. DFT calculations suggest that the anti-diastereomer is 2 kcal/mol more stable than the syn.
30. eq values are an average of three runs; all values deviated by <15% of the average value. See Supporting Information for details.
31. 1/2 > 10 h.
32. Hydroformylation of 3 leads to spontaneous formation of lactols under the reaction conditions. Because the lactols have an additional stereocenter, they are oxidized to the lactones for ease of analysis and isolation.
33. Hydroformylation of the methyl ether of 3 with 2b leads to a linear:branched ratio of 74:26, demonstrating the necessity of a free alcohol for branch selectivity. See Supporting Information for details.
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