A Method for the Protection of Lactones and Esters against Nucleophilic Attack

Journal of the American Chemical Society

Volumn 95, Issue 17, 1973, Pages 5829-5831

  Corey, E J ^a   Beames, David J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947085066     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00798a100     Document Type: Letter

References (11)

1. For a review of such protection see J. F. W. McOmie, Advtm. Ora. Chem., 3, 191 (1963);
2. J. F. W. McOmie, “Protective Groups in Organic Chemistry,” Plenum Press, London, 1973.
3. For background information sec R. H. De Wolfe, “Cuibolic Ortho Acid Derivatives,” Academic Press, New York, N. Y., 1978, Chapters 1 and 6.
4. Two methods for the conversion of lactones to ortho esters have been described by the Meerwein school: (a) the reaction with boron trifluoride and an oxirane to give 1,3-dioxolane derivatives [K. Boden-benner, Justus Liebigs Ann. Chem., 623, 183 (1959)], and
5. the reaction with a trialkyloxonium salt followed by treatment with an alkoxide salt [H. Meerwein, P. Borner, O. Fuchs, H. J. Saase, H. Schrodt, and J. Spille, Chem. Ber., 89, 2060 (1967)]. The former method requires the use of a strongly acidic reagent and affords at best only moderate yields; the latter suffers from limitations of scope and efficiency.
6. A number of methods which are applicable to thioketals (e.g., 1,3-dithianes) can be mentioned in this regard including Hg-+-HgO or N-halosuccinimide [E. J. Corey and B. W. Erickson, J. Org. Chem., 36, 3553 (1971);
7. E. Vedejs and P. L. Fuchs, J. Org. Chem., 36, 366 (1971)],
8. chlor-amine-T [D. W. Emerson and H. Wynberg, Tetrahedron Lett., 3445 (1971)], Ce(IV)
9. [T.-L. Ho, H. C. Ho, and C. M. Wong, J. Chem. Soc., Chem. Commun., 791 (1972)], and
10. CH.il or FSOiCHi [M. Fetizon and M. Jurion, J. Chem. Soc., Chem. Commun., 382 (1972)].
11. E. J. Corey, Z. Arnold, and J. Hutton, Tetrahedron Lett., 307 (1970).