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)