Ortho versus adjacent-benzylic directed lithiations of substituted N,N-diethylbenzamides

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1335-1338

  Court, John J ^a,c   Hlasta, Dennis J ^a,b  

^a EASTMAN KODAK COMPANY   (United States)

^b R W JOHNSON PHARMACEUTICAL RES I   (United States)

^c VERTEX PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZAMIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS;

EID: 0029874183     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00016-0     Document Type: Article

References (19)

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2. P. Beak and V. Snieckus Acc. Chem. Res. 1982, 15, 306. N. S. Narasimhan and R. S. Mali Synthesis 1983, 957. V. Snieckus Chem. Rev. 1990, 90, 879.
3. P. Beak and V. Snieckus Acc. Chem. Res. 1982, 15, 306. N. S. Narasimhan and R. S. Mali Synthesis 1983, 957. V. Snieckus Chem. Rev. 1990, 90, 879.
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9. C-C: 1, 5.8, 14.4 kcal/mol; 4, 0.56, 14.3 kcal/mol; 2a, < 0.05, 15.6 kcal/mol; 5, < 0.07, 15.6 kcal/mol.
10. F. Johnson Chem. Rev. 1968, 68, 375. F. Johnson and S.K. Malhotra J. Am. Chem. Soc. 1965, 87, 5492, 5493.
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14. 13
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17. Unpublished results. Private communicaton from P. Mark Henrichs, Laszlo L. Musza, and Charles A. Rodger of Sterling Winthrop Inc.
18. 25NO: C, 77.68; H, 10.19; N, 5.66. Found: C, 77.69; H, 10.27; N, 5.64.
19. 25NO: C, 77.68; H, 10.19; N, 5.66. Found: C, 77.71; H, 10.26; N, 5.61.