Corrigendum to “A tandem enol silane Formation-Mukaiyama aldol reaction mediated by TMSOTf” [Tetrahedron Lett. 48 (2007) 3559–3562](S0040403907005424)(10.1016/j.tetlet.2007.03.088);A tandem enol silane formation-Mukaiyama aldol reaction mediated by TMSOTf

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3559-3562

  Downey, C Wade ^a   Johnson, Miles W ^a  

^a UNIVERSITY OF RICHMOND   (United States)

Author keywords

Enol silane; Mukaiyama aldol; Silyl triflate; Silyl trifluoromethanesulfonate

Indexed keywords

AMINE; BASE; KETONE DERIVATIVE; MESYLIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CATALYSIS; CATALYST; MUKAIYAMA REACTION; OZONOLYSIS; POLYMERIZATION; QUANTUM YIELD; REACTION ANALYSIS;

EID: 34247161351     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2018.01.088     Document Type: Erratum

References (27)

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10. Evans and co-workers have documented the use of silylating reagents in conjunction with Lewis acid-catalyzed aldol reactions, but there is significant evidence that these reactions do not occur via a Mukaiyama aldol pathway. See:. Evans D.A., Tedrow J.S., Shaw J.T., and Downey C.W. J. Am. Chem. Soc. 124 (2002) 392-393
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14. A similar, intramolecular reaction with an ester enolate has recently been reported by Hoye:. Hoye T.R., Dvornikovs V., and Sizova E. Org. Lett. 8 (2006) 5191-5194
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18. Lewis base-catalyzed Mukaiyama aldol reactions are known. For example, see:. Denmark S.E., and Fan Y. J. Am. Chem. Soc. 124 (2002) 4233-4235
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20. (a) No further reaction was observed after 24 h; (b) NMR experiments suggest that Hunig's base and TMSOTf form an adduct under the reaction conditions.
21. No product was observed when TBAI was mixed with acetophenone enol silane and benzaldehyde for 24 h, eliminating the possibility of a pure Lewis base-catalyzed reaction. Likewise, no aldol product was observed when Hunig's base was replaced with TBAI in the tandem enol silane formation-Mukaiyama aldol reaction.
22. These results with TBAI are very similar to Bosnich's results with TBAOTf. See Ref. 5.
23. No product was observed with TMSCl.
24. 3N.
25. For recent examples of the synthesis of the silyl ketene acetal derived from ethyl acetate by treatment with LiHMDS and TMSCl, see:. Oisaki K., Suto Y., Kanai M., and Shibasaki M. J. Am. Chem. Soc. 125 (2003) 5644-5645
26. Ding F., Kopach M.E., Sabat M., and Harman W.D. J. Am. Chem. Soc. 124 (2002) 13080-13087
27. 1H NMR. In order to remove the TBS group, the initial adduct was treated with trifluoroacetic acid rather than HCl.