Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 8, 1978 - Issue 1
363
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

The Alkylation of Ketone Enolates in the Presence of Triethanolamineborate. Control of Polyalkylation

&
Pages 9-14 | Received 06 Sep 1977, Published online: 06 Dec 2006

References

  • c. f. Herbert O. House . 1965 . “ chapter 7 ” . In Modern Synthetic Reactions , 163 New York : W. A. Benjamin, Inc. .
  • House , H. O. and Kramar , V. 1963 . J. Org. Chem. , 28 : 3362
  • Stork , G. , Rosen , P. , Goldman , N. , Coombs , R. V. and Tsuji , J. 1965 . J. Amer. Chem. Soc. , 87 : 275
  • Tardella , P. A. 1969 . Tetrahedron Lett. , 14 : 1117 Tardella has reported that alkylation of ketone enolates in the presence of tri‐n‐butyltin chloride or triethylaluminum leads to decreased amounts of polyalkylation:
  • Brown , H. C. and Fletcher , E. A. 1951 . J. Amer. Chem. Soc. , 73 : 2808
  • Ketone enolates were generated by the addition of the ketone to a solution of Lithium diisopropyl‐amide (LDA) THF at 20°C
  • O‐Alkylation has been reported to be a serious competing reaction for ketone alkylations in dimethyl‐sulfoxide solution.8 It is possible that the recovered starting ketone is due to the hydrolysis of the O‐alkylated product during work‐up
  • 175 Ref. 1, and papers cited therein
  • Caine , D. 1964 . J. Org. Chem. , 29 : 1868 See also H. O. House and B. M. Trost, J. Org. Chem., 30, 1341 (1965)

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.