References
- Liu , H. J. and Lai , H. K. 1979 . Tetrahedron Lett. , : 1193
- Hauser , S. R. and Hudson , B. E. 1942 . Org. Reactions , 1 : 274 For reviews, see; J. P. Schaefer and J. J. Bloomfield, ibid., 15, 1 (1967)
- See ref. 4 for examples of synthetic applications of the β-keto thiolester group
- Liu , H. J. , Lai , H. K. and Attah-Poku , S. K. 1979 . Tetrahedron Lett. , : 4121
- Liu , H. J. , Attah-Poku , S. K. and Lai , H. K. 1979 . Synth. Commun. , 9 : 883
- All new compounds were adequately characterized by spectro-scopic methods and by exact mass measurement and/or elemental analysis. Yields given are for isolated products
- A similar rationale has been used to account for the regio-selectivity observed for Dieckmann condensation.2
- Prepared in situ using sodium hydride
- This compound was prepared in 80% yield by the alkylation of 2-ethylthiocarbonyl cyclohexanone with ethyl bromoacetate using the reported procedure.4
- It is pertinent to point out that similar isomerization has been occasionally used for the preparation of the γ-alkyl β-keto esters from the α-substituted isomers.11,12 These transformations however require longer reaction time under considerably more drastic conditions (alkoxide in refluxing alcohol or xylene) and often suffer from operational complexity and/or low yield of products
- Vul'fson , N. W. and Zaretskii , V. I. 1959 . J. Gen. Chem. USSR , 29 : 2704
- Sisido , K. , Utimoto , K. and Isida , T. 1964 . J. Org. Chem. , 29 : 2781
- We are grateful to Natural Science and Engineering Research Council of Canada and the University of Alberta for financial support