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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 5
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Original Articles

Preparation of Silylated Esters, Lactones, and Amides

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Pages 359-365 | Received 28 Apr 1975, Published online: 06 Dec 2006

References

  • 1973–74 . Johnson and Johnson Fellow
  • Hudrlik , P. F. and Peterson , D. 1972 . Tetrahedron Lett. , : 1785 Tetrahedron Lett., 1133 (1974); P. F. Hudrlik and D. Peterson, J. Am. Chem. Soc., 97, 1464 (1975). See also R. A. Ruden and B. L. Gaffney, Syn. Commun., 5, 15 (1975)
  • Shimoji , K. , Taguchi , H. , Oshima , K. , Yamamoto , H. and Nozaki , H. 1974 . J. Am. Chem. Soc. , 96 : 1620
  • Hartzell , S. L. , Sullivan , D. F. and Rathke , M. W. 1974 . Tetrahedron Lett. , : 1403
  • Taguchi , H. , Shimoji , K. , Yamamoto , H. and Nozaki , H. 1974 . Bull. Chem. Soc. Japan , 47 : 2529 For the use of a similar method to prepare unsaturated nitriles, see
  • Ojima , I. , Kumagai , M. and Nagai , Y. 1974 . Tetrahedron Lett. , : 4005
  • Baukov , Yu. I. and Lutsenko , I. F. 1970 . Organomet. Chem. Rev. A , 6 : 355 For a review of α-silyl carbonyl compounds, see
  • Hance , C. R. and Hauser , C. R. 1953 . J. Am. Chem. Soc. , 75 : 994
  • Krüger , C. R. and Rochow , E. G. 1964 . J. Organomet. Chem. , 1 : 476
  • Fessenden , R. J. and Fessenden , J. S. 1967 . J. Org. Chem. , 32 : 3535
  • Rühlmann , K. and Kuhrt , G. 1968 . Angew. Chem., Int. Ed. Engl. , 7 : 809
  • Ainsworth , C. , Chen , F. and Kuo , Y.-N . 1972 . J. Organomet. Chem. , 46 : 59
  • Ainsworth , C. and Kuo , Y.-N . 1972 . J. Organomet. Chem. , 46 : 73
  • Rathke , M. W. and Sullivan , D. F. 1973 . Syn. Commun. , 3 : 67
  • Rasmussen , J. K. and Hassner , A. 1974 . J. Org. Chem. , 39 : 2558
  • Reactions of silylated ester enolates with aldehydes and ketones have been reported; see ref 3
  • Professor P. A. Grieco (Pittsburgh) has independently prepared α-alkylidene -γ-lactones by this method; P. A. Grieco, personal communication
  • Pinder , A. R. 1952 . J. Chem. Soc. , : 2236
  • Klebe , J. F. , Bush , J. B. Jr. and Lyons , J. E. 1964 . J. Am. Chem. Soc. , 86 : 4400 Only two examples are reported. O-Silylation of the enolate of phenylacetyl piperidide was observed by C-silylation of a lactam enolate was found by B. M. Trost and R. A. Kunz, J. Org. Chem., 39, 2475 (1974)
  • Maslii , L. K. and Dobroserdova , I. L. 1967 . J. Gen. Chem. USSR , 37 : 2430
  • Lutsenko , I. F. , Baukov , Yu. I. , Kostyuk , A. S. , Savelyeva , N. I. and Krysina , V. K. 1969 . J. Organomet. Chem. , 17 : 241
  • Kostyuk , A. S. , Baukov , Yu. I. and Lutsenko , I. F. 1970 . J. Gen. Chem. USSR , 40 : 598
  • Cole , Q. P. U. S. Patent . 2776306 . 1957 . Chem. Abstr., 51, 7402d (1957). Nitrile anions also frequently silylate at carbon; for example, see
  • Llonch , J.-P and Frainnet , E. 1973 . C. R. Acad. Sci., Ser. C. , 276 : 1803
  • Watt , D. S. 1974 . Syn. Commun. , 4 : 127 and references cited therein. See also
  • Brenner , S. and Bovete , M. 1974 . Tetrahedron Lett. , : 1377
  • Skorokhodov , S. S. , Ershova , S. G. , Mikhailova , N. V. and Vansheidt , A. A. 1961 . J. Gen. Chem. USSR , 31 : 3382

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