Diastereoselective radical alkylations of alkyl aryl sulfoxides

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8387-8390

  Zahouily, Mohamed ^a,b   Caron, Giulia ^c   Carrupt, Pierre Alain ^c   Knouzi, Nourdine ^b   Renaud, Philippe ^a  

^a UNIVERSITY OF FRIBOURG   (Switzerland)

^b FACULTÉ DES SCIENCES BEN M SIK   (Morocco)

^c UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16044373582     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01899-0     Document Type: Article

References (23)

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2. 1. Curran, D. P. Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I. Eds.; Pergamon: Oxford, 1991; Vol. 4, pp 715-777. Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bond; Pergamon ed.; Oxford, 1988.
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12. 4. Several groups have reported highly stereoselective reactions using 1-sulfinylated radicals bearing an extra stabilizing groups such as esters, amides and ketones: Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc. Chem. Commun. 1991, 1151-1152. Snider, B. B.; Wan, B. Y-F.; Buckman, B. O.; Foxman, B. M. J. Org. Chem. 1991, 56, 328-334. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871-874.
13. 4. Several groups have reported highly stereoselective reactions using 1-sulfinylated radicals bearing an extra stabilizing groups such as esters, amides and ketones: Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc. Chem. Commun. 1991, 1151-1152. Snider, B. B.; Wan, B. Y-F.; Buckman, B. O.; Foxman, B. M. J. Org. Chem. 1991, 56, 328-334. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871-874.
14. 4. Several groups have reported highly stereoselective reactions using 1-sulfinylated radicals bearing an extra stabilizing groups such as esters, amides and ketones: Beckwith, A. L. J.; Hersperger, R.; White, J. M. J. Chem. Soc. Chem. Commun. 1991, 1151-1152. Snider, B. B.; Wan, B. Y-F.; Buckman, B. O.; Foxman, B. M. J. Org. Chem. 1991, 56, 328-334. De Mesmaeker, A.; Waldner, A.; Hoffmann, P.; Mindt, T. Synlett 1993, 871-874.
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18. 1H-NMR spectra have been used to attribute the synlanti configurations, the signal of the syn isomers are shifted to lower field: 2a (syn 6.17/5.53; anti 6.28/5.70); 2b (syn 6.19/5.54; anti 6.39/5.83); 2c (syn 6.13/5.49; anti 6.30/5.73); 2d(syn 6.11/5.44; anti 6.39/5.88); 2e (syn 6.03/5.50; anti 6.18/5.62); 2f (syn 6.07/5.45; anti 6.34/5.88); 2g (syn 5.78/5.37; anti 6.04/5.40).
19. 9. The semi-empirical calculations were performed with the AM1 hamiltonian using the Spartan4.0 software (Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715 USA, © 1995, Wavefunction, Inc.). The standard convergence criteria were used and the minima characterized by the analysis of the Hessian matrix. Full details will be published in a forthcoming full paper.
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