Novel approach to the synthesis of enantioenriched sulfoxides. Highly diastereoselective alkylation of sulfenate anions with 1,4-asymmetric induction

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3619-3622

  Sandrinelli, Franck ^a   Perrio, Stéphane ^a   Averbuch Pouchot, Marie Thérèse ^b  

^a UNIVERSITÉ DE CAEN   (France)

^b UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0041702197     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026563s     Document Type: Article

References (62)

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34. Use of these substrates has previously been reported in the synthesis of two naturally occurring compounds, (a) Shimazaki, M.; Ohta, A. Synthesis 1992, 957-958.
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41. Ollis, W. D.; Rey, M.; Sutherland, I. O. J. Chem. Soc., Perkin Trans. 1 1983, 1009-1027.
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43. Disulfide can be easily removed by washing with diethyl ether. Compound 2 was obtained in 33% yield through addition of a stoichimetric amount of p-TsOH, whereas no thiol at all was isolated with methanolic HCl.
44. The oxidation is completely chemoselective at sulfur. No N-oxidation byproducts were detected in the final reaction mixture.
45. On stirring (1R)-N,N-dimethyl-1-phenylethylamine with methyl iodide at room temperature in THF, precipitation occurred rapidly. The solid product was identified as the ammonium salt and was isolated in quantitative yield after a reaction time of 2 h.
46. For the preparation of the piperidinyl thiol, see: (a) Tsuge, H.; Okano, T.; Eguchi, S.; Kimoto, H. J. Chem. Soc., Perkin Trans. 1 1997, 1581-1586.
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48. 1H NMR of the crude mixture and was consistent with that of the purified product (±2%). The most diagnostically useful signals are those of the methine and methyl protons of the dimethylaminoethyl side chain.
49. For examples in enolate chemistry, see: (a) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624-1654.
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55. Chini, M.; Crotti, P.; Flippin, L. A.; Macchia, F. J. Org. Chem. 1990, 55, 4265-4272.
56. The oxidizing agents tested were peracids, hydrogen peroxide, potassium persulfate, and sodium perborate.
57. The methyl sulfide was prepared in 86% yield from (1R)-N,N-dimethyl-1-phenylethylamine by ortho-lithiation and trapping with dimethyl disulfide (see ref 7b).
58. In contrast, oxidation with the more classical benzaldehyde-derived oxaziridine, namely, (±)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine, gave a complex mixture in which sulfoxides 3a and 4a could be detected (yield < 40%). Among the side products, 1-methylsulfanyl-2-vinyibenzene was produced in 28% yield, with spectral data in agreement with those reported: Bianchini, C.; Frediani, P.; Herrera, V.; Jiménez, M. V.; Meli, A.; Rincón, L.; Sánchez-Delgado, R.; Vizza, F. J. Am. Chem. Soc. 1995, 117, 4333-4346. The formation of this styrene derivative can be interpreted in terms of a competitive oxidation on nitrogen followed by Cope elimination and illustrates the difference of oxidizing power of the two oxaziridines. For precedents, see: Christian, P. W. N.; Gibson (née Thomas), S. E.; Gil, R.; Jones, C. V.; Marcos, C. F.; Prechtl, F.; Wierzchleyski, A. T. Red. Trav. Chim. Pays-Bas 1995, 114, 195-202. For a review of the use of this oxaziridine, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742.
59. In contrast, oxidation with the more classical benzaldehyde-derived oxaziridine, namely, (±)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine, gave a complex mixture in which sulfoxides 3a and 4a could be detected (yield < 40%). Among the side products, 1-methylsulfanyl-2-vinyibenzene was produced in 28% yield, with spectral data in agreement with those reported: Bianchini, C.; Frediani, P.; Herrera, V.; Jiménez, M. V.; Meli, A.; Rincón, L.; Sánchez-Delgado, R.; Vizza, F. J. Am. Chem. Soc. 1995, 117, 4333-4346. The formation of this styrene derivative can be interpreted in terms of a competitive oxidation on nitrogen followed by Cope elimination and illustrates the difference of oxidizing power of the two oxaziridines. For precedents, see: Christian, P. W. N.; Gibson (née Thomas), S. E.; Gil, R.; Jones, C. V.; Marcos, C. F.; Prechtl, F.; Wierzchleyski, A. T. Red. Trav. Chim. Pays-Bas 1995, 114, 195-202. For a review of the use of this oxaziridine, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742.
60. In contrast, oxidation with the more classical benzaldehyde-derived oxaziridine, namely, (±)-trans-2-(phenylsulfonyl)-3-phenyloxaziridine, gave a complex mixture in which sulfoxides 3a and 4a could be detected (yield < 40%). Among the side products, 1-methylsulfanyl-2-vinyibenzene was produced in 28% yield, with spectral data in agreement with those reported: Bianchini, C.; Frediani, P.; Herrera, V.; Jiménez, M. V.; Meli, A.; Rincón, L.; Sánchez-Delgado, R.; Vizza, F. J. Am. Chem. Soc. 1995, 117, 4333-4346. The formation of this styrene derivative can be interpreted in terms of a competitive oxidation on nitrogen followed by Cope elimination and illustrates the difference of oxidizing power of the two oxaziridines. For precedents, see: Christian, P. W. N.; Gibson (née Thomas), S. E.; Gil, R.; Jones, C. V.; Marcos, C. F.; Prechtl, F.; Wierzchleyski, A. T. Red. Trav. Chim. Pays-Bas 1995, 114, 195-202. For a review of the use of this oxaziridine, see: Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742.
61. No X-ray crystallographic structural data for sulfenate salts has been reported in the literature. However, we believe that lithium is coordinated to oxygen rather than to sulfur, on the basis of the accepted concepts of hard and soft acids and bases: Pearson, R. G. Hard and Soft Acids and Bases; Sisler, H. H., Ed.; Dowden, Hutchinson and Ross: Stroudsburg, 1973.
62. Bond lengths of around 2 Å have previously been reported in sparteine-mediated reactions of lithium reagents: Hoppe, D.; Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282-2316.