Catalytic diastereoselective sulfimidation of diaryl sulfides and application of chiral sulfimides to asymmetric allylic alkylation

Chirality

Volumn 12, Issue 5-6, 2000, Pages 299-312

  Takada, Hiroya ^a   Oda, Masamitsu ^a   Oyamada, Arihiro ^a   Ohe, Kouichi ^a   Uemura, Sakae ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Allylic substitution; Chiral oxazoline; Chloramine T trihydrate; Copper catalyst; N ptosylsulfimide

Indexed keywords

OXAZOLINE DERIVATIVE; SULFIDE; TOSYLCHLORAMIDE SODIUM;

ALKYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; CHIRALITY; ENANTIOMER; OPTICAL ROTATION; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0034079352     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<299::AID-CHIR2>3.0.CO;2-S     Document Type: Article

References (60)

1. (a) Komatsu N, Nishibayashi Y, Sugita T, Uemura S. Catalytic asymmetric oxidation of sulfides to sulfoxides using R-(+)-binaphthol. Tetrahedron Lett 1992;33:5391-5394.
2. (b) Komatsu N, Hashizume M, Sugita T, Uemura S. Catalytic asymmetric oxidation of sulfides to sulfoxides with tert-butyl hydroperoxide using binaphthol as a chiral auxiliary. J Org Chem 1993;58:4529-4533.
3. (a) Takada H, Nishibayashi Y, Ohe K, Uemura S. Novel asymmetric catalytic synthesis of sulfimides. Chem Commun 1996;931-932.
4. (b) Takada H, Nishibayashi Y, Ohe K, Uemura S, Baird CP, Sparey TJ, Taylor PC. Catalytic asymmetric sulfimidation. J Org Chem 1997;62: 6512-6518.
5. Miyake Y, Takada H, Ohe K, Uemura S. Catalytic asymmetric sulfimidation of 1,3-dithianes. J Chem Soc Perkin Trans 1998;1:2373-2376.
6. Nishibayashi Y, Ohe K, Uemura S. The first example of enantioselective carbenoid addition to organochalcogen atoms: application to [2,3]sigmatropic rearrangement of allylic chalcogen ylides. J Chem Soc Chem Commun 1995;1245-1246.
7. (a) Bower JF, Martin CJ, Rawson DJ, Slawin AMZ, Williams JMJ. Diastereoselective conversion of sulfides into sulfoxides. 1,5-and 1,6-Asymmetric induction. J Chem Soc Perkin Trans 1996;1:333-342.
8. (b) Bower JF, Williams JMJ. Diastereoselective oxidation of aryl sulfides. Tetrahedron Lett 1994;35:7111-7114.
9. (a) Allen JV, Bower JF, Williams JMJ. Enantioselective palladium catalyzed aliylic substitution. Electronic and steric effects of the ligand. Tetrahedron: Asymmetry 1994;5:1895-1898.
10. (b) Williams JMJ. The ups and downs of allylpalladium complexes in catalysis. Synlett 1996;705-710.
11. Zhang J, Takahashi T, Koizumi T. Optically pure alkoxychlorosulfuranes. Synthesis and transformation to chiral sulfoxides, N-p-tosylsulfilimines, and sulfonium ylides. Heterocycles 1997;44:325-339.
12. Cassel S, Plessis I, Wessel HP, Rollin P. First synthesis of anomeric sulfimides - efficient glycosyl donors. Tetrahedron Lett 1998;39: 8097-8100.
13. Celentano G, Colonna S. Highly enantioselective synthesis of dialkyl and alkyl aryl N-tosylsulfimides. Chem Commun 1998;701-702.
14. Takada H, Ohe K, Uemura S. Preliminary communication: Catalytic diastereoselective imidation of diaryl sulfides bearing a chiral oxazolinyl moiety with chloramine-T trihydrate. Angew Chem Int Ed 1999;38: 1288-1289.
15. Allen JV, Dawson GJ, Frost CG, Williams JMJ, Coote SJ. Preparation of novel sulfur and phosphorus containing oxazolines as ligands for asymmetric catalysis. Tetrahedron 1994;50:799-808.
16. (a) Rebstock MC, Crooks MH, Controulis J, Bartz QR. Chloramphenicol (chloromycetin). IV. Chemical studies. J Am Chem Soc 1949;71: 2458-2462.
17. (b) Kollonitsch J, Hajós A. Untersuchungen auf dem gebiete des chloramphenicols, III. Die racemisierung von Lg-(+)-threo-1-p-nitrophenyl-2-amino-1,3-dioxypropan. Acta Chim Acad Sci Hung 1955; 8:271-282.
18. (a) Gilchrist TL, Moody CJ. The chemistry of sulfilimines. Chem Rev 1977;77:409-436.
19. (b) Johnson CR. Sulphoximides. In: Barton DHR, Ollis WD, editors. Comprehensive organic chemistry. New York: Pergamon; 1979. p 215-222.
20. (c) Koval IV. Progress in the chemistry of sulphilimines. Russ Chem Rev 1990;59:819-831 and references therein.
21. (a) Barton DHR, Britten-Kelly MR, Ferreira D. Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 9. New reagents for amination of the ethylenic linkage. J Chem Soc Perkin Trans 1978; 1:1090-1100.
22. (b) Ando T, Minakata S, Ryu I, Komatsu M. Nitrogen atom transfer to alkenes utilizing Chloramine-T as a nitrogen source. Tetrahedron Lett 1998;39:309-312.
23. Klundt IL. Anhydrous Chloramine-T. Chem Eng News 1977;55(No. 49):56.
24. Frost CG, Howarth J, Williams JMJ. Selectivity in palladium catalyzed allylic substitution. Tetrahedron: Asymmetry 1992;3:1089-1122.
25. (a) Day J, Cram DJ. Stereochemistry of nucleophilic substitution at sulfur. Stereospecific synthesis of an optically active sulfilimine. J Am Chem Soc 1965;87:4398-4399.
26. (b) Cram DJ, Day J, Rayner DR, von Schriltz DM, Duchamp DJ, Garwood DC. Stereochemistry of sulfur compounds. I. Stereochemical reaction cycles involving an open chain sulfoxide, sulfimide, and sulfoximide. J Am Chem Soc 1970;92:7369-7384.
27. Tsujihara K, Furukawa N, Oae K, Oae S. Sulfimine. I. Synthesis and formation mechanism. Bull Chem Soc Jpn 1969;42:2631-2635.
28. Damin B, Garapon J, Sillion B. Reactions du N-chloroparatoluene-sulfonamidate de sodium (Chloramine T) sur les olefines en milieu acide organique. Tetrahedron Lett 1980;21:1709-1710; A convenient synthesis of chlorohydrins using Chloramine T. Synthesis 1981;22: 362-363.
29. Damin B, Garapon J, Sillion B. Reactions du N-chloroparatoluene-sulfonamidate de sodium (Chloramine T) sur les olefines en milieu acide organique. Tetrahedron Lett 1980;21:1709-1710; A convenient synthesis of chlorohydrins using Chloramine T. Synthesis 1981;22: 362-363.
30. Yoshimura T, Omata T, Furukawa N, Oae S. Preparation and physical and chemical properties of "Free" sulfilimines. J Org Chem 1976;41: 1728-1733.
31. (a) Trost BM, Brickner SJ. Palladium-assisted macrocyclization approach to cytochalasins: a synthesis of antibiotic A26771B. J Am Chem Soc 1983;105:568-575.
32. (b) Hayashi T, Yamamoto A, Hagiwara T, Ito Y. Modification of optically active ferrocenylphosphine ligands for palladium-catalyzed asymmetric allylic alkylation. Tetrahedron Lett 1986; 27:191-194.
33. (c) von Matt P, Pfaltz A. Chiral phosphinoaryldihydrooxazoles as ligands in asymmetric catalysis: Pd-catalyzed allylic substitution. Angew Chem Int Ed Engl 1993;32:566-568.
34. (d) Sennhenn P, Gabler B, Helmchen G. Enantiomerically pure cycloalkenylacetic acid derivatives via Pd-catalyzed asymmetric allylic alkylation and subsequent enantiomeric enrichment via iodolactones. Tetrahedron Lett 1994;35:8595-8598.
35. (e) Trost BM, Van Vranken DL. Asymmetric transition metal-catalyzed allylic substitution. Chem Rev 1996;96:395-422.
36. (f) Vyskocil S, Smrcina M, Hanus V, Polásek M, Kocovsky P. Derivatives of 2-amino-2′-diphenylphosphino-1,1′-binaphthyl (MAP) and their application in asymmetric palladium (0)-catalyzed allylic substitution. J Org Chem 1998;63:7738-7748 and references therein.
37. (a) Frost CG, Williams JMJ. Enantioselective palladium-catalyzed allylic substitution with thienyloxazoline ligands. Tetrahedron Lett 1993; 34:2015-2018.
38. (b) Dawson GJ, Martin CJ, Williams JMJ, Coote SJ. Sulfides tethered to oxazolines: ligands for enantioselective catalysis. Tetrahedron Lett 1993;34:7793-7796.
39. (c) Frost CG, Williams JMJ. Enantioselective palladium catalyzed allylic substitution with sulfur-containing oxazoline ligands. Tetrahedron: Asymmetry 1993;4:1785-1788.
40. (d) Frost CG, Williams JMJ. Enantiomerically pure acetals as ligands for asymmetric catalysis. Synlett 1994;551-552.
41. (e) Allen JV, Coote SJ, Dawson GJ, Frost CG, Martin CJ, Williams JMJ. Palladium-catalyzed asymmetric allylic substitution: a ligand design incorporating steric and electronic effects. J Chem Soc Perkin Trans 1994;1:2065-2072.
42. (a) Chelucci G, Cabras MA. Enantioselective palladium catalyzed allylic substitution with sulfur-containing pyridine ligands. Tetrahedron: Asymmetry 1996;7:965-966.
43. (b) Chelucci G, Berta D, Saba A. Chiral sulfoxides and sulfides tethered to pyridines as ligands for enantioselective catalysis: palladium catalyzed allylic substitution and addition of diethylzinc to benzaldehyde. Tetrahedron 1997;53:3843-3848.
44. (a) Barbaro P, Currao A, Herrmann J, Nesper R, Pregosin PS, Salzmann R. Chiral P,S-ligands based on β-D-thioglucose tetraacetate. Palladium(II) complexes and allylic alkylation. Organometallics 1996;15: 1879-1888.
45. (b) Albinati A, Pregosin PS, Wick K. A new P,S-chiral auxiliary derived from thioglucose. X-ray structure of a palladium 1,3-diphenylallyl complex with a strongly rotated allyl ligand. Organometallics 1996;15:2419-2421.
46. (c) Boog-Wick K, Pregosin PS, Trabesinger G. New chiral N,S-ligands based on oxazoline-thioglucose donors. Palladium(II)-catalyzed enantioselective allylic alkylation. Organometallics 1998;17:3254-3264.
47. (a) Hiroi K, Suzuki Y. Chiral β-amino sulfoxides as chiral ligands in palladium-catalyzed asymmetric allylations. Heterocycles 1997;46:77-81.
48. (b) Hiroi K, Suzuki Y. New chiral o-(phosphinoamido)phenyl sulfoxide ligands in palladium-catalyzed asymmetric allylic alkylations. Tetrahedron Lett 1998;39:6499-6502.
49. (c) Hiroi K, Suzuki Y, Abe I, Hasegawa Y, Suzuki K. Chiral sulfoxide ligands bearing nitrogen atoms as stereocontrollable coordinating elements in palladium-catalyzed asymmetric allylic alkylation. Tetrahedron: Asymmetry 1998; 9:3797-3817.
50. Morimoto T, Tachibana K, Achiwa K. Asymmetric reactions catalyzed by chiral metal complexes. Part 78. Chiral thio imidazoline ligands for palladium-catalyzed asymmetric allylation. Synlett 1997;783-785.
51. Chesney A, Bryce MR, Chubb RWJ, Batsanov AS, Howard JAK. Chiral ferrocenyl-oxazolines incorporating thioether units: effective ligands for palladium-catalyzed allylic substitution. Tetrahedron: Asymmetry 1997;8:2337-2346.
52. Anderson JC, James DS, Mathias JP. Sulfur-imine mixed donor chelate ligands for asymmetric catalysis: enantioselective allylic alkylation. Tetrahedron: Asymmetry 1998;9:753-756.
53. You S-L, Zhou Y-G, Hou X-L, Dai L-X. Enantioselective palladium catalyzed allylic substitution with thioether derivatives of ferrocenyl-oxazoline and the role of planar chirality in this reaction. Chem Commun 1998;2765-2766.
54. Koning B, Meetsma A, Kellogg RM. Chiral nonracemic pyridine thiols and thioethers applied in palladium-catalyzed allylic substitution. An example of near-perfect enantioselection. J Org Chem 1998;63:5533-5540.
55. 2-symmetric chiral bis-sulfoxide ligand and its palladium (II) complex. Tetrahedron Lett 1995;36:8035-8038.
56. Bolm C, Kaufmann D, Zehnder M, Neuburger M. Optically active sulfoximines in enantioselective palladium catalysis. Tetrahedron Lett 1996;37:3985-3988.
57. Yamada Y, Yamamoto T, Okawara M. Synthesis and reaction of new type I-N ylide, N-tosyliminoiodinane. Chem Lett 1975;361-362.
58. McKonnon MJ, Meyer AI, Drauz K, Schwarm M. A convenient reduction of amino acids and their derivatives. J Org Chem 1993;58:3568-3571.
59. 2 complex. Chem Ber 1991;124:1173-1180.
60. Schumacker DP, Clark JE, Murphy BL, Fischer PA. An efficient synthesis of florenicol. J Org Chem 1990;55:5291-5294.