REFERENCES
- Herrmann , J. L. , Kieczykowski , G. R. and Schlessinger , R. H. 1973 . Tetrahedron Lett. , : 2433 This original procedure used a 1:1 complex of LDA:HMPA as the base for the deconjugative alkylation.
- Kuwajima , I. and Urabe , H. 1993 . Organic Syntheses , Edited by: Freeman , J. P. Vol. VIII , 486 New York : Wiley . Collect., This report describes a modification of the procedure reported in ref. 1 which uses 1:1 LDA:DMPU as the base for the deconjugative alkylation
- For safety reasons, DMPU was substituted for the HMPA used in the original procedure. When the deconjugative alkylations were run on the same scale in HMPA, products 5 and 6 were produced in 62% and 85% purified yields (unoptimized). Our lower yield of 5 in both solvents, compared with the earlier report of 90% by Schlessinger, likely results from mixing and localized heating problems associated with the larger scale used in the current reactions
- Mukhopadhyay , T. and Seebach , D. 1982 . Helv. Chim. Acta , 65 : 385
- Crossland , R. K. and Servis , K. L. 1970 . J. Org. Chem. , 35 : 3195
- Tufariello , J. J. , Mullen , G. B. , Tegeler , J. J. , Trybulski , E. J. , Wong , S. C. and Ali , S. A. 1979 . J. Am. Chem. Soc. , 101 : 2435
- This reaction also proceeded in HMPA but, for safety reasons, DMPU was used. The yield was essentially the same in both solvents