An umpolung sulfoxide reagent as α-hydroxy and α-chloro benzyl carbanion equivalents

Tetrahedron Letters

Volumn 43, Issue 37, 2002, Pages 6537-6540

  Volonterio, Alessandro ^b   Bravo, Pierfrancesco ^a,b   Zanda, Matteo ^a  

^a CNR   (Italy)

^b POLITECNICO DI MILANO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 [(N METHYL)CARBAMOYL]PHENYLBENZYLSULFOXIDE; ANION; BENZYL DERIVATIVE; BROMINE DERIVATIVE; FUNCTIONAL GROUP; REAGENT; SULFOXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; DIASTEREOISOMER; RACEMIC MIXTURE; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0037048473     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01435-1     Document Type: Article

References (29)

1. For a review, see: (a) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. A., Ed.; Pergamon: New York, 1991; Vol. 3, pp. 193-205. See also: (b) Fernández-Megía, E.; Ley, S. V. Synlett 2000, 455-458 and references cited therein; (c) Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392-2398; (d) Deiters, A.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2000, 39, 2105-2107.
2. For a review, see: (a) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. A., Ed.; Pergamon: New York, 1991; Vol. 3, pp. 193-205. See also: (b) Fernández-Megía, E.; Ley, S. V. Synlett 2000, 455-458 and references cited therein; (c) Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392-2398; (d) Deiters, A.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2000, 39, 2105-2107.
3. For a review, see: (a) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. A., Ed.; Pergamon: New York, 1991; Vol. 3, pp. 193-205. See also: (b) Fernández-Megía, E.; Ley, S. V. Synlett 2000, 455-458 and references cited therein; (c) Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392-2398; (d) Deiters, A.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2000, 39, 2105-2107.
4. For a review, see: (a) Cheshire, D. R. In Comprehensive Organic Synthesis; Trost, B. A., Ed.; Pergamon: New York, 1991; Vol. 3, pp. 193-205. See also: (b) Fernández-Megía, E.; Ley, S. V. Synlett 2000, 455-458 and references cited therein; (c) Linderman, R. J.; Ghannam, A. J. Am. Chem. Soc. 1990, 112, 2392-2398; (d) Deiters, A.; Fröhlich, R.; Hoppe, D. Angew. Chem., Int. Ed. 2000, 39, 2105-2107.
5. Mark Dan
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12. To our knowledge the α-C-alkylation of ortho-carbamoyl-aryl alkyl sulfoxides has not been reported previously. For some reviews on the alkylation of metallated sulfoxides, see: (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835-871; (b) Solladié, G. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme: Stuttgart, 1995; Vol. E21b, pp. 1793-1815; (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998; (d) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
13. To our knowledge the α-C-alkylation of ortho-carbamoyl-aryl alkyl sulfoxides has not been reported previously. For some reviews on the alkylation of metallated sulfoxides, see: (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835-871; (b) Solladié, G. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme: Stuttgart, 1995; Vol. E21b, pp. 1793-1815; (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998; (d) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
14. To our knowledge the α-C-alkylation of ortho-carbamoyl-aryl alkyl sulfoxides has not been reported previously. For some reviews on the alkylation of metallated sulfoxides, see: (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835-871; (b) Solladié, G. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme: Stuttgart, 1995; Vol. E21b, pp. 1793-1815; (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998; (d) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
15. To our knowledge the α-C-alkylation of ortho-carbamoyl-aryl alkyl sulfoxides has not been reported previously. For some reviews on the alkylation of metallated sulfoxides, see: (a) Procter, D. J. J. Chem. Soc., Perkin Trans. 1 2000, 835-871; (b) Solladié, G. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme: Stuttgart, 1995; Vol. E21b, pp. 1793-1815; (c) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961-998; (d) Carreño, M. C. Chem. Rev. 1995, 95, 1717-1760.
16. 4, filtered and the solvent evaporated in vacuo. The residue was purified by flash-chromatography to give 8a (1.68 mmol, 577 mg) in 92% yield.
17. No reaction was observed in the following cases: without HMPA, replacing HMPA with TMEDA, or replacing BuLi with LDA, except in the case of BnBr which led to 8g with low stereocontrol (see Table 2 ).
18. The crystal structure of 8e will be published in a full paper.
19. 1 are likely to play a key role in the transition state.
20. Some alkyl halides, such as isobutyl-bromide and 2-bromomethyl-dioxolane reacted very sluggishly with α-substituted sulfoxides 1a,b.
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24. Cipollina J.A., Ruediger E.H., New J.S., Wire M.E., Shepherd T.A., Smith D.W., Yevich J.P. J. Med. Chem. 34:1991;3316-3328.
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26. . For a highly stereoselective lactonization with displacement of a sulfinyl group under Pummerer-type conditions, see: Casey M., Manage A.C., Murphy P.J. Tetrahedron Lett. 33:1992;965-968.
27. 4, filtered and the solvent evaporated in vacuo. The residue was purified by flash-chromatography to give 10b (0.17 mmol, 33 mg) in 71% yield and 5 (0.22 mmol, 36 mg, 92%).
28. Details on these products will be published in a forthcoming full paper.
29. 2 are produced, in analogy with the outcome of the Swern reaction.